BRPI0614343A2 - derivados de 3-sulfonilindazol substituìdo como ligantes de 5-hidroxitriptamina-6 - Google Patents

Info

Publication number

BRPI0614343A2

BRPI0614343A2 BRPI0614343-1A BRPI0614343A BRPI0614343A2 BR PI0614343 A2 BRPI0614343 A2 BR PI0614343A2 BR PI0614343 A BRPI0614343 A BR PI0614343A BR PI0614343 A2 BRPI0614343 A2 BR PI0614343A2

Authority

BR

Brazil

Prior art keywords

indazol

naphthylsulfonyl

oxy

ethyl

formula

Prior art date

2005-08-15

Links

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• Global Dossier
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• 239000011230 binding agent Substances 0.000 title abstract description 4
• DDJYYJIWIYUTRV-UHFFFAOYSA-N 3-sulfonylindazole Chemical class C1=CC=C2C(=S(=O)=O)N=NC2=C1 DDJYYJIWIYUTRV-UHFFFAOYSA-N 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 328
• 108091005435 5-HT6 receptors Proteins 0.000 claims abstract description 17
• 208000015114 central nervous system disease Diseases 0.000 claims abstract description 11
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 3
• -1 cycloetheroalkyl Chemical group 0.000 claims description 197
• 229910052757 nitrogen Inorganic materials 0.000 claims description 88
• 238000000034 method Methods 0.000 claims description 78
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 36
• 150000001412 amines Chemical class 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 33
• 238000006243 chemical reaction Methods 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 19
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 235000010288 sodium nitrite Nutrition 0.000 claims description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 13
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 10
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 208000035475 disorder Diseases 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical compound NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• NXQGEDVQXVTCDA-UHFFFAOYSA-N n,n-dimethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(C)C)=CC=CC2=C1 NXQGEDVQXVTCDA-UHFFFAOYSA-N 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• FFXYPUZNRSHAQG-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-2h-indazol-5-yl]-n-methylethanamine Chemical compound C12=CC(CCNC)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 FFXYPUZNRSHAQG-UHFFFAOYSA-N 0.000 claims description 5
• HDXBREGAPLXGIS-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]-n,n-dimethylethanamine Chemical compound C12=CC(OCCN(C)C)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 HDXBREGAPLXGIS-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 5
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 5
• NTWIXXNPWJCUKO-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]-n-ethylethanamine Chemical compound C12=CC(OCCNCC)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 NTWIXXNPWJCUKO-UHFFFAOYSA-N 0.000 claims description 4
• YRZHGGDYKODNJU-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]-n-methylethanamine Chemical compound C12=CC(OCCNC)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 YRZHGGDYKODNJU-UHFFFAOYSA-N 0.000 claims description 4
• LDXXPFIHTIGYPU-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(2-piperidin-1-ylethoxy)-2h-indazole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCN1CCCCC1 LDXXPFIHTIGYPU-UHFFFAOYSA-N 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 208000010877 cognitive disease Diseases 0.000 claims description 4
• VCHCBGQDIOIUSD-UHFFFAOYSA-N n-[2-(1-methyl-3-naphthalen-1-ylsulfonylindazol-5-yl)oxyethyl]propan-2-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NN(C)C4=CC=C(C=C43)OCCNC(C)C)=CC=CC2=C1 VCHCBGQDIOIUSD-UHFFFAOYSA-N 0.000 claims description 4
• ISLLLFJSCFDYNX-UHFFFAOYSA-N n-[2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethyl]propan-2-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCNC(C)C)=CC=CC2=C1 ISLLLFJSCFDYNX-UHFFFAOYSA-N 0.000 claims description 4
• FNRWMGYHMJLWDN-UHFFFAOYSA-N n-[2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]ethyl]propan-2-amine Chemical compound C12=CC(OCCNC(C)C)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 FNRWMGYHMJLWDN-UHFFFAOYSA-N 0.000 claims description 4
• ROYVCTNFSAPNLB-UHFFFAOYSA-N n-[3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propyl]cyclopropanamine Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCCNC1CC1 ROYVCTNFSAPNLB-UHFFFAOYSA-N 0.000 claims description 4
• UHISQLHPYWNPQW-UHFFFAOYSA-N n-ethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCNCC)=CC=CC2=C1 UHISQLHPYWNPQW-UHFFFAOYSA-N 0.000 claims description 4
• NCTFDQWFOOHFFC-UHFFFAOYSA-N n-methyl-2-(1-methyl-3-naphthalen-1-ylsulfonylindazol-5-yl)oxyethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NN(C)C4=CC=C(C=C43)OCCNC)=CC=CC2=C1 NCTFDQWFOOHFFC-UHFFFAOYSA-N 0.000 claims description 4
• BQHVXLWCYFWZGS-UHFFFAOYSA-N n-methyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCNC)=CC=CC2=C1 BQHVXLWCYFWZGS-UHFFFAOYSA-N 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• GISNOEZWSXUMJI-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-3-naphthalen-1-ylsulfonylindazol-7-yl]oxy-n-methylethanamine Chemical compound C1=2C(OCCNC)=CC=CC=2C(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=NN1CC1=CC=CC(Cl)=C1 GISNOEZWSXUMJI-UHFFFAOYSA-N 0.000 claims description 3
• PTCSHLCQBWNEIT-UHFFFAOYSA-N 3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]-n-propan-2-ylpropan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCNC(C)C)=CC=CC2=C1 PTCSHLCQBWNEIT-UHFFFAOYSA-N 0.000 claims description 3
• SDCUZMUHLPBVER-UHFFFAOYSA-N 3-naphthalen-1-ylsulfonyl-5-(3-pyrrolidin-1-ylpropoxy)-2h-indazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCCN1CCCC1 SDCUZMUHLPBVER-UHFFFAOYSA-N 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• FSUSRKMBYMEREP-UHFFFAOYSA-N n,n-diethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(CC)CC)=CC=CC2=C1 FSUSRKMBYMEREP-UHFFFAOYSA-N 0.000 claims description 3
• VUKPWKNVDTZIIO-UHFFFAOYSA-N n-[2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethyl]butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCNCCCC)=CC=CC2=C1 VUKPWKNVDTZIIO-UHFFFAOYSA-N 0.000 claims description 3
• MDTWXGWSXAWFTR-UHFFFAOYSA-N n-[2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethyl]cyclopropanamine Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCNC1CC1 MDTWXGWSXAWFTR-UHFFFAOYSA-N 0.000 claims description 3
• LKWUURPREMRAAG-UHFFFAOYSA-N n-[3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propyl]butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCNCCCC)=CC=CC2=C1 LKWUURPREMRAAG-UHFFFAOYSA-N 0.000 claims description 3
• LQTIUQBMJBAWMD-UHFFFAOYSA-N n-[3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propyl]cyclopentanamine Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCCNC1CCCC1 LQTIUQBMJBAWMD-UHFFFAOYSA-N 0.000 claims description 3
• KFBPBGMNYWGBTK-UHFFFAOYSA-N n-ethyl-n-methyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(C)CC)=CC=CC2=C1 KFBPBGMNYWGBTK-UHFFFAOYSA-N 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• PSHLDNLWBBFDFD-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-3-naphthalen-1-ylsulfonyl-7-(3-pyrrolidin-1-ylpropoxy)indazole Chemical compound ClC1=CC=CC(CN2C3=C(OCCCN4CCCC4)C=CC=C3C(=N2)S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=C1 PSHLDNLWBBFDFD-UHFFFAOYSA-N 0.000 claims description 2
• HMYUFCVGTBDGEL-UHFFFAOYSA-N 2-[(5-fluoro-3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]-n,n-dimethylethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=C(F)C=C(C=4NN=3)OCCN(C)C)=CC=CC2=C1 HMYUFCVGTBDGEL-UHFFFAOYSA-N 0.000 claims description 2
• MKDGUGOLAULVEG-UHFFFAOYSA-N 2-[(5-fluoro-3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]-n-methylethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=C(F)C=C(C=4NN=3)OCCNC)=CC=CC2=C1 MKDGUGOLAULVEG-UHFFFAOYSA-N 0.000 claims description 2
• LJNYDPDAMOHONR-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-1-methylindazol-7-yl]oxy-n-methylethanamine Chemical compound N=1N(C)C=2C(OCCNC)=CC=CC=2C=1S(=O)(=O)C1=CC=CC=C1 LJNYDPDAMOHONR-UHFFFAOYSA-N 0.000 claims description 2
• JJOUYXALLGKCDX-UHFFFAOYSA-N 3-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)-n-propan-2-ylpropan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)CCCNC(C)C)=CC=CC2=C1 JJOUYXALLGKCDX-UHFFFAOYSA-N 0.000 claims description 2
• WQVVPQOPYLVTPT-UHFFFAOYSA-N 3-naphthalen-1-ylsulfonyl-4-(2-pyrrolidin-1-ylethoxy)-2h-indazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C=12)=NNC2=CC=CC=1OCCN1CCCC1 WQVVPQOPYLVTPT-UHFFFAOYSA-N 0.000 claims description 2
• AWZSBFZVBKOHCU-UHFFFAOYSA-N 3-naphthalen-1-ylsulfonyl-7-(2-pyrrolidin-1-ylethoxy)-2h-indazole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=CC=C2)=NNC1=C2OCCN1CCCC1 AWZSBFZVBKOHCU-UHFFFAOYSA-N 0.000 claims description 2
• QSLGLGHRVKEICG-UHFFFAOYSA-N 4-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)-n-propan-2-ylbutan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)CCCCNC(C)C)=CC=CC2=C1 QSLGLGHRVKEICG-UHFFFAOYSA-N 0.000 claims description 2
• 206010003805 Autism Diseases 0.000 claims description 2
• 208000020706 Autistic disease Diseases 0.000 claims description 2
• 208000012239 Developmental disease Diseases 0.000 claims description 2
• 201000010374 Down Syndrome Diseases 0.000 claims description 2
• 208000001914 Fragile X syndrome Diseases 0.000 claims description 2
• 208000006011 Stroke Diseases 0.000 claims description 2
• RQOKMHCTFHXXMM-UHFFFAOYSA-N n'-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)ethane-1,2-diamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)NCCN)=CC=CC2=C1 RQOKMHCTFHXXMM-UHFFFAOYSA-N 0.000 claims description 2
• QXPWRAXEWDBKHX-UHFFFAOYSA-N n'-(3-naphthalen-1-ylsulfonyl-2h-indazol-6-yl)ethane-1,2-diamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C4=CC=C(C=C4NN=3)NCCN)=CC=CC2=C1 QXPWRAXEWDBKHX-UHFFFAOYSA-N 0.000 claims description 2
• QYCVGIKLACULSQ-UHFFFAOYSA-N n'-(3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)ethane-1,2-diamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=CC=C(C=4NN=3)NCCN)=CC=CC2=C1 QYCVGIKLACULSQ-UHFFFAOYSA-N 0.000 claims description 2
• KIIXTMKHCQBIED-UHFFFAOYSA-N n,n-dimethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=CC=C(C=4NN=3)OCCN(C)C)=CC=CC2=C1 KIIXTMKHCQBIED-UHFFFAOYSA-N 0.000 claims description 2
• VCOPJXGPLYGQDT-UHFFFAOYSA-N n,n-dimethyl-3-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)CCCN(C)C)=CC=CC2=C1 VCOPJXGPLYGQDT-UHFFFAOYSA-N 0.000 claims description 2
• GQCRISDKILEPEY-UHFFFAOYSA-N n,n-dimethyl-4-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)CCCCN(C)C)=CC=CC2=C1 GQCRISDKILEPEY-UHFFFAOYSA-N 0.000 claims description 2
• NAAMMAQETSMMJD-UHFFFAOYSA-N n-(3-naphthalen-1-ylsulfonyl-2h-indazol-6-yl)-3-piperidin-1-ylpropanamide Chemical compound C=1C=C2C(S(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=NNC2=CC=1NC(=O)CCN1CCCCC1 NAAMMAQETSMMJD-UHFFFAOYSA-N 0.000 claims description 2
• MQWHAZNMNZNWCX-UHFFFAOYSA-N n-[2-[3-(benzenesulfonyl)-2h-indazol-7-yl]ethyl]cyclopropanamine Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1=CC=C2)=NNC1=C2CCNC1CC1 MQWHAZNMNZNWCX-UHFFFAOYSA-N 0.000 claims description 2
• AAXRJUUYWCWJBW-UHFFFAOYSA-N n-[2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]ethyl]cyclopentanamine Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCNC1CCCC1 AAXRJUUYWCWJBW-UHFFFAOYSA-N 0.000 claims description 2
• RHOSAQSWTNFUCW-UHFFFAOYSA-N n-[2-[[3-(benzenesulfonyl)-2h-indazol-7-yl]oxy]ethyl]butan-1-amine Chemical compound N=1NC=2C(OCCNCCCC)=CC=CC=2C=1S(=O)(=O)C1=CC=CC=C1 RHOSAQSWTNFUCW-UHFFFAOYSA-N 0.000 claims description 2
• BOMDVAWDCALISF-UHFFFAOYSA-N n-[3-[3-(benzenesulfonyl)-2h-indazol-5-yl]propyl]cyclopropanamine Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2CCCNC1CC1 BOMDVAWDCALISF-UHFFFAOYSA-N 0.000 claims description 2
• LJXLTOUCKSNHLN-UHFFFAOYSA-N n-ethyl-2-(1-methyl-3-naphthalen-1-ylsulfonylindazol-5-yl)oxyethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NN(C)C4=CC=C(C=C43)OCCNCC)=CC=CC2=C1 LJXLTOUCKSNHLN-UHFFFAOYSA-N 0.000 claims description 2
• NKQVYPRRVFKJKV-UHFFFAOYSA-N n-ethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCNCC)=CC=CC2=C1 NKQVYPRRVFKJKV-UHFFFAOYSA-N 0.000 claims description 2
• XUUXCWWCIUMXON-UHFFFAOYSA-N n-ethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=CC=C(C=4NN=3)OCCNCC)=CC=CC2=C1 XUUXCWWCIUMXON-UHFFFAOYSA-N 0.000 claims description 2
• VMZSUVXRPPNISM-UHFFFAOYSA-N n-ethyl-2-[(5-fluoro-3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=C(F)C=C(C=4NN=3)OCCNCC)=CC=CC2=C1 VMZSUVXRPPNISM-UHFFFAOYSA-N 0.000 claims description 2
• UBZDXQGFVPTXDZ-UHFFFAOYSA-N n-ethyl-3-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)CCCNCC)=CC=CC2=C1 UBZDXQGFVPTXDZ-UHFFFAOYSA-N 0.000 claims description 2
• ABFPREJKBODYNG-UHFFFAOYSA-N n-ethyl-4-(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)CCCCNCC)=CC=CC2=C1 ABFPREJKBODYNG-UHFFFAOYSA-N 0.000 claims description 2
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