JP2012505895A5

JP2012505895A5 -

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Publication number: JP2012505895A5
Authority: JP; Japan
Prior art keywords: indole; methyl; benzodioxin; dihydrospiro; furo
Prior art date: 2009-10-13
Legal status : Granted

Application number

JP2011532189A

Other languages

English (en)

Japanese (ja)

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JP5554337B2 (ja

JP2012505895A (ja

Filing date

2009-10-13

Publication date

2012-11-08

2009-10-13 Application filed filed Critical

2009-10-13 Priority claimed from PCT/US2009/060537 external-priority patent/WO2010045251A2/en

2012-03-08 Publication of JP2012505895A publication Critical patent/JP2012505895A/ja

2012-11-08 Publication of JP2012505895A5 publication Critical patent/JP2012505895A5/ja

2014-07-23 Application granted granted Critical

2014-07-23 Publication of JP5554337B2 publication Critical patent/JP5554337B2/ja

Status Expired - Fee Related legal-status Critical Current

2029-10-13 Anticipated expiration legal-status Critical

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-1 (3-carboxy) benzyl Chemical group 0.000 claims description 655
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 215
125000005605 benzo group Chemical group 0.000 claims description 213
150000001875 compounds Chemical class 0.000 claims description 93
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 92
239000000203 mixture Substances 0.000 claims description 54
150000003839 salts Chemical class 0.000 claims description 38
239000012453 solvate Substances 0.000 claims description 38
239000000651 prodrug Substances 0.000 claims description 37
229940002612 prodrug Drugs 0.000 claims description 37
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
208000002193 Pain Diseases 0.000 claims description 26
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 23
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
241000124008 Mammalia Species 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 20
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 16
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 11
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 11
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 9
239000005711 Benzoic acid Substances 0.000 claims description 7
235000010233 benzoic acid Nutrition 0.000 claims description 7
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 7
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 6
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 5
108010052164 Sodium Channels Proteins 0.000 claims description 5
102000018674 Sodium Channels Human genes 0.000 claims description 5
230000001404 mediated effect Effects 0.000 claims description 5
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
QDYZUZGMRVLKJB-QHCPKHFHSA-N (8s)-1'-[(5-hydroxypyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound N1=CC(O)=CC=C1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O QDYZUZGMRVLKJB-QHCPKHFHSA-N 0.000 claims description 4
XGYVWWLZOMQVRF-QHCPKHFHSA-N (8s)-1'-[[3-(trifluoromethyl)pyridin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=CN=C1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O XGYVWWLZOMQVRF-QHCPKHFHSA-N 0.000 claims description 4
ZVVSYCLIZDVVNX-UHFFFAOYSA-N 1'-(2,1,3-benzoxadiazol-5-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1CCOC(C=C23)=C1C=C3OCC12C2=CC=CC=C2N(CC2=CC3=NON=C3C=C2)C1=O ZVVSYCLIZDVVNX-UHFFFAOYSA-N 0.000 claims description 4
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
206010015150 Erythema Diseases 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
125000000597 dioxinyl group Chemical group 0.000 claims description 4
231100000321 erythema Toxicity 0.000 claims description 4
TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 4
150000002500 ions Chemical class 0.000 claims description 4
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
201000006417 multiple sclerosis Diseases 0.000 claims description 4
208000033808 peripheral neuropathy Diseases 0.000 claims description 4
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 4
SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 claims description 3
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 3
230000000996 additive effect Effects 0.000 claims description 3
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 3
125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
IKLODGBPSWONQT-QGZVFWFLSA-N (3r)-spiro[1h-indole-3,8'-3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine]-2-one Chemical compound O1CCOC(C=C23)=C1C=C3OC[C@]12C2=CC=CC=C2NC1=O IKLODGBPSWONQT-QGZVFWFLSA-N 0.000 claims description 2
IKLODGBPSWONQT-KRWDZBQOSA-N (3s)-spiro[1h-indole-3,8'-3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine]-2-one Chemical compound O1CCOC(C=C23)=C1C=C3OC[C@@]12C2=CC=CC=C2NC1=O IKLODGBPSWONQT-KRWDZBQOSA-N 0.000 claims description 2
OVACCWHGLATOEQ-JLCFBVMHSA-N (8r)-1'-[[(2r)-1,4-dioxan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C([C@@]1(C2=CC=3OCCOC=3C=C2OC1)C1=CC=CC=C11)N1C[C@@H]1COCCO1 OVACCWHGLATOEQ-JLCFBVMHSA-N 0.000 claims description 2
OVACCWHGLATOEQ-RCDICMHDSA-N (8r)-1'-[[(2s)-1,4-dioxan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C([C@@]1(C2=CC=3OCCOC=3C=C2OC1)C1=CC=CC=C11)N1C[C@H]1COCCO1 OVACCWHGLATOEQ-RCDICMHDSA-N 0.000 claims description 2
KFOPOGCFEPXXRU-XMMPIXPASA-N (8r)-1'-[[2-(trifluoromethyl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=CC=C1CN1C2=CC=CC=C2[C@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O KFOPOGCFEPXXRU-XMMPIXPASA-N 0.000 claims description 2
GAXCBEUTBLMRBB-HSZRJFAPSA-N (8r)-1'-[[3-(trifluoromethyl)pyridin-2-yl]methyl]spiro[4,7-dihydrofuro[2,3-g][1,3]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=CN=C1CN1C2=CC=CC=C2[C@]2(C3=CC=4OCOCC=4C=C3OC2)C1=O GAXCBEUTBLMRBB-HSZRJFAPSA-N 0.000 claims description 2
GOYMEMMMRYGXSI-JOCHJYFZSA-N (8r)-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1C(C(F)(F)F)=CC=C1CN1C2=CC=CC=C2[C@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O GOYMEMMMRYGXSI-JOCHJYFZSA-N 0.000 claims description 2
PGSAVXKGTOBDQF-NRFANRHFSA-N (8s)-1'-(2-oxobutyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CC(=O)CC)C(=O)[C@]11C2=CC(OCCO3)=C3C=C2OC1 PGSAVXKGTOBDQF-NRFANRHFSA-N 0.000 claims description 2
XTDQALUCJKCSDI-QFIPXVFZSA-N (8s)-1'-(pyrazin-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C([C@]1(C2=CC=3OCCOC=3C=C2OC1)C1=CC=CC=C11)N1CC1=CN=CC=N1 XTDQALUCJKCSDI-QFIPXVFZSA-N 0.000 claims description 2
JAKJUFIVIMMNFQ-QFIPXVFZSA-N (8s)-1'-(pyrimidin-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C([C@]1(C2=CC=3OCCOC=3C=C2OC1)C1=CC=CC=C11)N1CC1=NC=CC=N1 JAKJUFIVIMMNFQ-QFIPXVFZSA-N 0.000 claims description 2
MQSGSLDBWKEUJX-QHCPKHFHSA-N (8s)-1'-[(2-methoxypyrimidin-5-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=NC(OC)=NC=C1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O MQSGSLDBWKEUJX-QHCPKHFHSA-N 0.000 claims description 2
NOZQYLPTSXNBQI-QHCPKHFHSA-N (8s)-1'-[(3-fluoropyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1=CC=CN=C1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O NOZQYLPTSXNBQI-QHCPKHFHSA-N 0.000 claims description 2
OEVQPVZMBDMQHH-HKBQPEDESA-N (8s)-1'-[(4-phenylmethoxyphenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C([C@]1(C2=CC=3OCCOC=3C=C2OC1)C1=CC=CC=C11)N1CC(C=C1)=CC=C1OCC1=CC=CC=C1 OEVQPVZMBDMQHH-HKBQPEDESA-N 0.000 claims description 2
ULLXBGNIWJHCSC-QHCPKHFHSA-N (8s)-1'-[(5-fluoropyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound N1=CC(F)=CC=C1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O ULLXBGNIWJHCSC-QHCPKHFHSA-N 0.000 claims description 2
CJZDIDWIJJFYFO-QHCPKHFHSA-N (8s)-1'-[(5-fluoropyridin-3-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1=CN=CC(CN2C3=CC=CC=C3[C@@]3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 CJZDIDWIJJFYFO-QHCPKHFHSA-N 0.000 claims description 2
KFMXUACXWOJTPR-QFIPXVFZSA-N (8s)-1'-[2-(2-methoxyethoxy)ethyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCOCCOC)C(=O)[C@]11C2=CC(OCCO3)=C3C=C2OC1 KFMXUACXWOJTPR-QFIPXVFZSA-N 0.000 claims description 2
OVACCWHGLATOEQ-PEBXRYMYSA-N (8s)-1'-[[(2r)-1,4-dioxan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C([C@]1(C2=CC=3OCCOC=3C=C2OC1)C1=CC=CC=C11)N1C[C@@H]1COCCO1 OVACCWHGLATOEQ-PEBXRYMYSA-N 0.000 claims description 2
OVACCWHGLATOEQ-FPTDNZKUSA-N (8s)-1'-[[(2s)-1,4-dioxan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C([C@]1(C2=CC=3OCCOC=3C=C2OC1)C1=CC=CC=C11)N1C[C@H]1COCCO1 OVACCWHGLATOEQ-FPTDNZKUSA-N 0.000 claims description 2
FGPWLFKYOWLCQS-LGGPFLRQSA-N (8s)-1'-[[(2s)-4-benzylmorpholin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C([C@H](OCC1)CN2C([C@]3(C4=CC=5OCCOC=5C=C4OC3)C3=CC=CC=C32)=O)N1CC1=CC=CC=C1 FGPWLFKYOWLCQS-LGGPFLRQSA-N 0.000 claims description 2
ODIWUDOCYQAYHM-WNSKOXEYSA-N (8s)-1'-[[(2s)-4-methylmorpholin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1N(C)CCO[C@@H]1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O ODIWUDOCYQAYHM-WNSKOXEYSA-N 0.000 claims description 2
OIKFNAVSRGCHFA-FPTDNZKUSA-N (8s)-1'-[[(2s)-morpholin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C([C@]1(C2=CC=3OCCOC=3C=C2OC1)C1=CC=CC=C11)N1C[C@@H]1CNCCO1 OIKFNAVSRGCHFA-FPTDNZKUSA-N 0.000 claims description 2
KFOPOGCFEPXXRU-DEOSSOPVSA-N (8s)-1'-[[2-(trifluoromethyl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=CC=C1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O KFOPOGCFEPXXRU-DEOSSOPVSA-N 0.000 claims description 2
XLXZWMOWPFLTHF-DEOSSOPVSA-N (8s)-1'-[[3-(difluoromethyl)pyridin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)C1=CC=CN=C1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O XLXZWMOWPFLTHF-DEOSSOPVSA-N 0.000 claims description 2
GOYMEMMMRYGXSI-QFIPXVFZSA-N (8s)-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1C(C(F)(F)F)=CC=C1CN1C2=CC=CC=C2[C@@]2(C3=CC=4OCCOC=4C=C3OC2)C1=O GOYMEMMMRYGXSI-QFIPXVFZSA-N 0.000 claims description 2
XMOFGZSGUNSQJM-QFIPXVFZSA-N (8s)-1'-pentylspiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCCCC)C(=O)[C@]11C2=CC(OCCO3)=C3C=C2OC1 XMOFGZSGUNSQJM-QFIPXVFZSA-N 0.000 claims description 2
ODFVBUTWATUWOH-UHFFFAOYSA-N 1'-(1,3-benzothiazol-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1CCOC(C=C23)=C1C=C3OCC12C2=CC=CC=C2N(CC=2SC3=CC=CC=C3N=2)C1=O ODFVBUTWATUWOH-UHFFFAOYSA-N 0.000 claims description 2
SXTHACPTDSPJLD-UHFFFAOYSA-N 1'-(2,1,3-benzothiadiazol-5-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1CCOC(C=C23)=C1C=C3OCC12C2=CC=CC=C2N(CC2=CC3=NSN=C3C=C2)C1=O SXTHACPTDSPJLD-UHFFFAOYSA-N 0.000 claims description 2
LSGFIUFVCLXHFV-UHFFFAOYSA-N 1'-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1CCOC(C=C23)=C1C=C3OCC12C2=CC=CC=C2N(CC=2C=C3OCCOC3=CC=2)C1=O LSGFIUFVCLXHFV-UHFFFAOYSA-N 0.000 claims description 2
IJIGBJQKGJGOMD-UHFFFAOYSA-N 1'-(2-cyclopropylethyl)spiro[4,7-dihydrofuro[2,3-g][1,3]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCOCC=4C=C3OC2)C(=O)N1CCC1CC1 IJIGBJQKGJGOMD-UHFFFAOYSA-N 0.000 claims description 2
OWWWUUICTRNNOB-UHFFFAOYSA-N 1'-(2-ethoxyethyl)spiro[4,7-dihydrofuro[2,3-g][1,3]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCOCC)C(=O)C11C2=CC(OCOC3)=C3C=C2OC1 OWWWUUICTRNNOB-UHFFFAOYSA-N 0.000 claims description 2
ZACBIMWTDRTJDM-UHFFFAOYSA-N 1'-(3-hydroxypropyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCCO)C(=O)C11C2=CC(OCCO3)=C3C=C2OC1 ZACBIMWTDRTJDM-UHFFFAOYSA-N 0.000 claims description 2
QGIMMENNPRBVCW-UHFFFAOYSA-N 1'-(3-methoxypropyl)spiro[4,7-dihydrofuro[2,3-g][1,3]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCCOC)C(=O)C11C2=CC(OCOC3)=C3C=C2OC1 QGIMMENNPRBVCW-UHFFFAOYSA-N 0.000 claims description 2
AVDLVCJUWCGJTQ-UHFFFAOYSA-N 1'-(3-methylbutyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCC(C)C)C(=O)C11C2=CC(OCCO3)=C3C=C2OC1 AVDLVCJUWCGJTQ-UHFFFAOYSA-N 0.000 claims description 2
ADNRFSHEPKQEMO-UHFFFAOYSA-N 1'-(4-fluorophenyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=CC(F)=CC=C1N1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O ADNRFSHEPKQEMO-UHFFFAOYSA-N 0.000 claims description 2
CZEVVNKETHDYNZ-UHFFFAOYSA-N 1'-(4-methoxybutyl)spiro[4,7-dihydrofuro[2,3-g][1,3]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCCCOC)C(=O)C11C2=CC(OCOC3)=C3C=C2OC1 CZEVVNKETHDYNZ-UHFFFAOYSA-N 0.000 claims description 2
NVXASOYHLYOBAF-UHFFFAOYSA-N 1'-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1CCOC(C=C23)=C1C=C3OCC12C2=CC=CC=C2N(CC2=CN3N=CN=C3C=C2)C1=O NVXASOYHLYOBAF-UHFFFAOYSA-N 0.000 claims description 2
OIKFNAVSRGCHFA-UHFFFAOYSA-N 1'-(morpholin-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1CNCCO1 OIKFNAVSRGCHFA-UHFFFAOYSA-N 0.000 claims description 2
FFAHBBWUJIIYHD-UHFFFAOYSA-N 1'-(oxan-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1CCCCO1 FFAHBBWUJIIYHD-UHFFFAOYSA-N 0.000 claims description 2
XZFRZLIXGXJSNW-UHFFFAOYSA-N 1'-(oxan-4-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1CCOCC1 XZFRZLIXGXJSNW-UHFFFAOYSA-N 0.000 claims description 2
XTPHLACNTNTUEA-UHFFFAOYSA-N 1'-(piperidin-4-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1CCNCC1 XTPHLACNTNTUEA-UHFFFAOYSA-N 0.000 claims description 2
MXAAAOCSCQPXHP-UHFFFAOYSA-N 1'-(pyridin-2-ylmethyl)-4'-quinolin-3-ylspiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC(C=3C=C4C=CC=CC4=NC=3)=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1=CC=CC=N1 MXAAAOCSCQPXHP-UHFFFAOYSA-N 0.000 claims description 2
GSTHQCXJZUKAQK-UHFFFAOYSA-N 1'-(pyridin-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1=CC=CC=N1 GSTHQCXJZUKAQK-UHFFFAOYSA-N 0.000 claims description 2
PTNDREICWNNZGI-UHFFFAOYSA-N 1'-(pyridin-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1=CC=CC=N1 PTNDREICWNNZGI-UHFFFAOYSA-N 0.000 claims description 2
DYKMTZCGGLUWEL-UHFFFAOYSA-N 1'-(pyridin-3-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1=CC=CN=C1 DYKMTZCGGLUWEL-UHFFFAOYSA-N 0.000 claims description 2
JAKJUFIVIMMNFQ-UHFFFAOYSA-N 1'-(pyrimidin-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC1=NC=CC=N1 JAKJUFIVIMMNFQ-UHFFFAOYSA-N 0.000 claims description 2
WPFIGTMAUCWGSI-UHFFFAOYSA-N 1'-[(1-methylbenzotriazol-5-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C1C2(C3=CC=4OCCOC=4C=C3OC2)C2=CC=CC=C2N1CC1=CC=C2N(C)N=NC2=C1 WPFIGTMAUCWGSI-UHFFFAOYSA-N 0.000 claims description 2
PIAVFRKVOZLJMT-UHFFFAOYSA-N 1'-[(1-methylpiperidin-4-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one;hydrochloride Chemical compound Cl.C1CN(C)CCC1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O PIAVFRKVOZLJMT-UHFFFAOYSA-N 0.000 claims description 2
XTOPFJHHFRCITI-UHFFFAOYSA-N 1'-[(1-propan-2-ylpiperidin-4-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one;hydrochloride Chemical compound Cl.C1CN(C(C)C)CCC1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O XTOPFJHHFRCITI-UHFFFAOYSA-N 0.000 claims description 2
MMGYNTINVQEMJO-UHFFFAOYSA-N 1'-[(2,2-difluorocyclopropyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1(F)CC1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O MMGYNTINVQEMJO-UHFFFAOYSA-N 0.000 claims description 2
VSVGXCUQRJZIJW-UHFFFAOYSA-N 1'-[(2,3-difluorophenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1=CC=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1F VSVGXCUQRJZIJW-UHFFFAOYSA-N 0.000 claims description 2
MXCZLKWSTVNFSL-UHFFFAOYSA-N 1'-[(2-chloro-4-fluorophenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound ClC1=CC(F)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O MXCZLKWSTVNFSL-UHFFFAOYSA-N 0.000 claims description 2
MQSGSLDBWKEUJX-UHFFFAOYSA-N 1'-[(2-methoxypyrimidin-5-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=NC(OC)=NC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O MQSGSLDBWKEUJX-UHFFFAOYSA-N 0.000 claims description 2
JGGWKGNMMYJOQI-UHFFFAOYSA-N 1'-[(2-oxo-1h-pyrimidin-5-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=NC(O)=NC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O JGGWKGNMMYJOQI-UHFFFAOYSA-N 0.000 claims description 2
AMBJTSAPNLPEHZ-UHFFFAOYSA-N 1'-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound S1C(C(C)C)=NC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 AMBJTSAPNLPEHZ-UHFFFAOYSA-N 0.000 claims description 2
KHIRHVLLVOQTLS-SVZXGPMESA-N 1'-[(2s)-2,3-dihydroxypropyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(C[C@H](O)CO)C(=O)C11C2=CC(OCCO3)=C3C=C2OC1 KHIRHVLLVOQTLS-SVZXGPMESA-N 0.000 claims description 2
QMXRTTANANAIRG-UHFFFAOYSA-N 1'-[(3,4-dimethoxyphenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=C(OC)C(OC)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O QMXRTTANANAIRG-UHFFFAOYSA-N 0.000 claims description 2
QMQUUPPMGWXQQH-UHFFFAOYSA-N 1'-[(3,5-difluorophenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1=CC(F)=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 QMQUUPPMGWXQQH-UHFFFAOYSA-N 0.000 claims description 2
RTPIEPHXILGMHA-UHFFFAOYSA-N 1'-[(3,5-difluoropyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1=CC(F)=CN=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O RTPIEPHXILGMHA-UHFFFAOYSA-N 0.000 claims description 2
UKPORLQBCFJXBM-UHFFFAOYSA-N 1'-[(3,5-dimethoxyphenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound COC1=CC(OC)=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 UKPORLQBCFJXBM-UHFFFAOYSA-N 0.000 claims description 2
ARHWCAGMSXZGBY-UHFFFAOYSA-N 1'-[(3-aminophenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound NC1=CC=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 ARHWCAGMSXZGBY-UHFFFAOYSA-N 0.000 claims description 2
VWFKZNFCPUMOAU-UHFFFAOYSA-N 1'-[(3-aminopyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one;hydrobromide Chemical compound Br.NC1=CC=CN=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O VWFKZNFCPUMOAU-UHFFFAOYSA-N 0.000 claims description 2
VKEKJHKQNWWZMH-UHFFFAOYSA-N 1'-[(3-chloropyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound ClC1=CC=CN=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O VKEKJHKQNWWZMH-UHFFFAOYSA-N 0.000 claims description 2
NOZQYLPTSXNBQI-UHFFFAOYSA-N 1'-[(3-fluoropyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1=CC=CN=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O NOZQYLPTSXNBQI-UHFFFAOYSA-N 0.000 claims description 2
HONLRWJLGFZVNA-UHFFFAOYSA-N 1'-[(3-morpholin-4-ylsulfonylphenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC(C=1)=CC=CC=1S(=O)(=O)N1CCOCC1 HONLRWJLGFZVNA-UHFFFAOYSA-N 0.000 claims description 2
RCXHHYOTGLDFKV-UHFFFAOYSA-N 1'-[(3-pyridin-3-yl-1,2-oxazol-5-yl)methyl]spiro[4,7-dihydrofuro[2,3-g][1,3]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCOCC=4C=C3OC2)C(=O)N1CC(ON=1)=CC=1C1=CC=CN=C1 RCXHHYOTGLDFKV-UHFFFAOYSA-N 0.000 claims description 2
SBSPEBZSLPRFQR-UHFFFAOYSA-N 1'-[(4,6-dimethoxypyrimidin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound COC1=CC(OC)=NC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=N1 SBSPEBZSLPRFQR-UHFFFAOYSA-N 0.000 claims description 2
FGPWLFKYOWLCQS-UHFFFAOYSA-N 1'-[(4-benzylmorpholin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC(OCC1)CN1CC1=CC=CC=C1 FGPWLFKYOWLCQS-UHFFFAOYSA-N 0.000 claims description 2
RKJUQBVIAKUOQL-UHFFFAOYSA-N 1'-[(4-fluoropyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1=CC=NC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 RKJUQBVIAKUOQL-UHFFFAOYSA-N 0.000 claims description 2
WMQXIXXFBRJKHN-UHFFFAOYSA-N 1'-[(4-hydroxyphenyl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=CC(O)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O WMQXIXXFBRJKHN-UHFFFAOYSA-N 0.000 claims description 2
HOCMDWYHUMSPMF-UHFFFAOYSA-N 1'-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CC1=NON=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O HOCMDWYHUMSPMF-UHFFFAOYSA-N 0.000 claims description 2
ODIWUDOCYQAYHM-UHFFFAOYSA-N 1'-[(4-methylmorpholin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1N(C)CCOC1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O ODIWUDOCYQAYHM-UHFFFAOYSA-N 0.000 claims description 2
AATDZSLIMWAAAG-UHFFFAOYSA-N 1'-[(4-propan-2-ylmorpholin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1N(C(C)C)CCOC1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O AATDZSLIMWAAAG-UHFFFAOYSA-N 0.000 claims description 2
LLFDIXJHWUBFBI-UHFFFAOYSA-N 1'-[(5-bromopyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound N1=CC(Br)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O LLFDIXJHWUBFBI-UHFFFAOYSA-N 0.000 claims description 2
XMDUDUQTYBKMCD-UHFFFAOYSA-N 1'-[(5-chloro-1-methylimidazol-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(Cl)=CN=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O XMDUDUQTYBKMCD-UHFFFAOYSA-N 0.000 claims description 2
TVQLRQRWRYOXSN-UHFFFAOYSA-N 1'-[(5-chloro-1-methylimidazol-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one;hydrochloride Chemical compound Cl.CN1C(Cl)=CN=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O TVQLRQRWRYOXSN-UHFFFAOYSA-N 0.000 claims description 2
ULLXBGNIWJHCSC-UHFFFAOYSA-N 1'-[(5-fluoropyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound N1=CC(F)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O ULLXBGNIWJHCSC-UHFFFAOYSA-N 0.000 claims description 2
CJZDIDWIJJFYFO-UHFFFAOYSA-N 1'-[(5-fluoropyridin-3-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC1=CN=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 CJZDIDWIJJFYFO-UHFFFAOYSA-N 0.000 claims description 2
SZYOKJBIAMAUNJ-UHFFFAOYSA-N 1'-[(5-morpholin-4-ylpyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC(N=C1)=CC=C1N1CCOCC1 SZYOKJBIAMAUNJ-UHFFFAOYSA-N 0.000 claims description 2
VWRKPSYVSVTBSI-UHFFFAOYSA-N 1'-[(6-aminopyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound NC1=CC=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=N1 VWRKPSYVSVTBSI-UHFFFAOYSA-N 0.000 claims description 2
CQRMIHIIXNETGL-UHFFFAOYSA-N 1'-[(6-aminopyridin-3-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=NC(N)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O CQRMIHIIXNETGL-UHFFFAOYSA-N 0.000 claims description 2
OAYBJQOAVWNPGH-UHFFFAOYSA-N 1'-[(6-chloropyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound ClC1=CC=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=N1 OAYBJQOAVWNPGH-UHFFFAOYSA-N 0.000 claims description 2
QNMBOSUGXIRONQ-UHFFFAOYSA-N 1'-[(6-methoxypyridin-3-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=NC(OC)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O QNMBOSUGXIRONQ-UHFFFAOYSA-N 0.000 claims description 2
VRCKAOBSBSZQBN-UHFFFAOYSA-N 1'-[(6-methylpyridin-2-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CC1=CC=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=N1 VRCKAOBSBSZQBN-UHFFFAOYSA-N 0.000 claims description 2
CZPVUGDGUXZYRF-UHFFFAOYSA-N 1'-[(6-morpholin-4-ylpyridin-3-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC(C=N1)=CC=C1N1CCOCC1 CZPVUGDGUXZYRF-UHFFFAOYSA-N 0.000 claims description 2
IQVBQXSKAMELQT-UHFFFAOYSA-N 1'-[(6-oxo-1h-pyridin-3-yl)methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC=1C=CC(=O)NC=1 IQVBQXSKAMELQT-UHFFFAOYSA-N 0.000 claims description 2
KFMXUACXWOJTPR-UHFFFAOYSA-N 1'-[2-(2-methoxyethoxy)ethyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2N(CCOCCOC)C(=O)C11C2=CC(OCCO3)=C3C=C2OC1 KFMXUACXWOJTPR-UHFFFAOYSA-N 0.000 claims description 2
OMUZUTOEKBUYKB-ADRQNKRLSA-N 1'-[[(2r)-oxolan-2-yl]methyl]spiro[2,5,6,7-tetrahydrofuro[3,2-g]chromene-3,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4CCCOC=4C=C3OC2)C(=O)N1C[C@H]1CCCO1 OMUZUTOEKBUYKB-ADRQNKRLSA-N 0.000 claims description 2
UJJVMJZVKCALNG-HNNQXCQYSA-N 1'-[[(2r)-oxolan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1C[C@H]1CCCO1 UJJVMJZVKCALNG-HNNQXCQYSA-N 0.000 claims description 2
KFOPOGCFEPXXRU-UHFFFAOYSA-N 1'-[[2-(trifluoromethyl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O KFOPOGCFEPXXRU-UHFFFAOYSA-N 0.000 claims description 2
LWWMADWTBQCDLD-UHFFFAOYSA-N 1'-[[2-(trifluoromethyl)pyridin-3-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=NC=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O LWWMADWTBQCDLD-UHFFFAOYSA-N 0.000 claims description 2
GDDUYBIKGWVGIP-UHFFFAOYSA-N 1'-[[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CC1=NOC(C=2C=C(CN3C4=CC=CC=C4C4(C5=CC=6OCCOC=6C=C5OC4)C3=O)C=CC=2)=N1 GDDUYBIKGWVGIP-UHFFFAOYSA-N 0.000 claims description 2
ILHBWEJNJKPSRD-UHFFFAOYSA-N 1'-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1C(C)=NC(C=2C=C(CN3C4=CC=CC=C4C4(C5=CC=6OCCOC=6C=C5OC4)C3=O)C=CC=2)=N1 ILHBWEJNJKPSRD-UHFFFAOYSA-N 0.000 claims description 2
QIPTVNPPIMPECS-UHFFFAOYSA-N 1'-[[3-(trifluoromethyl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 QIPTVNPPIMPECS-UHFFFAOYSA-N 0.000 claims description 2
RJIJMNHTBSTQKM-UHFFFAOYSA-N 1'-[[3-(trifluoromethyl)pyrazin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=NC=CN=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O RJIJMNHTBSTQKM-UHFFFAOYSA-N 0.000 claims description 2
GAXCBEUTBLMRBB-UHFFFAOYSA-N 1'-[[3-(trifluoromethyl)pyridin-2-yl]methyl]spiro[4,7-dihydrofuro[2,3-g][1,3]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=CN=C1CN1C2=CC=CC=C2C2(C3=CC=4OCOCC=4C=C3OC2)C1=O GAXCBEUTBLMRBB-UHFFFAOYSA-N 0.000 claims description 2
QTZFADPTWARYQW-UHFFFAOYSA-N 1'-[[4-(3-amino-1h-pyrazol-5-yl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one;hydrochloride Chemical compound Cl.N1N=C(N)C=C1C(C=C1)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O QTZFADPTWARYQW-UHFFFAOYSA-N 0.000 claims description 2
ZHTBPXBZNOJDDU-UHFFFAOYSA-N 1'-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CC1=NOC(C=2C=CC(CN3C4=CC=CC=C4C4(C5=CC=6OCCOC=6C=C5OC4)C3=O)=CC=2)=N1 ZHTBPXBZNOJDDU-UHFFFAOYSA-N 0.000 claims description 2
YYRWVLAQFHQCKW-UHFFFAOYSA-N 1'-[[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1C(C)=NC(C=2C=CC(CN3C4=CC=CC=C4C4(C5=CC=6OCCOC=6C=C5OC4)C3=O)=CC=2)=N1 YYRWVLAQFHQCKW-UHFFFAOYSA-N 0.000 claims description 2
KTKSHDRPWKAAJL-UHFFFAOYSA-N 1'-[[4-(trifluoromethyl)-1,3-thiazol-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CSC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=N1 KTKSHDRPWKAAJL-UHFFFAOYSA-N 0.000 claims description 2
YUCYIUDMXCUFNX-UHFFFAOYSA-N 1'-[[4-(trifluoromethyl)pyridin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=NC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=C1 YUCYIUDMXCUFNX-UHFFFAOYSA-N 0.000 claims description 2
YAUIXVNOMZMOAG-UHFFFAOYSA-N 1'-[[4-(trifluoromethyl)pyridin-3-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=NC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O YAUIXVNOMZMOAG-UHFFFAOYSA-N 0.000 claims description 2
WAMMVSROMNSILC-UHFFFAOYSA-N 1'-[[5-(difluoromethyl)furan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1C(C(F)F)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O WAMMVSROMNSILC-UHFFFAOYSA-N 0.000 claims description 2
UHWWFRNTYZANQB-UHFFFAOYSA-N 1'-[[5-(dimethylamino)pyridin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound N1=CC(N(C)C)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O UHWWFRNTYZANQB-UHFFFAOYSA-N 0.000 claims description 2
HHSXDQCXLYHACO-UHFFFAOYSA-N 1'-[[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O1C(C(F)(F)F)=NC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=N1 HHSXDQCXLYHACO-UHFFFAOYSA-N 0.000 claims description 2
VWBJFLBSAMKBSM-UHFFFAOYSA-N 1'-[[5-(trifluoromethyl)pyridin-2-yl]methyl]spiro[4,7-dihydrofuro[2,3-g][1,3]benzodioxine-8,3'-indole]-2'-one Chemical compound N1=CC(C(F)(F)F)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCOCC=4C=C3OC2)C1=O VWBJFLBSAMKBSM-UHFFFAOYSA-N 0.000 claims description 2
RTOYYQOEDIWNEB-UHFFFAOYSA-N 1'-[[6-(benzhydrylideneamino)pyridin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1CC(N=1)=CC=CC=1N=C(C=1C=CC=CC=1)C1=CC=CC=C1 RTOYYQOEDIWNEB-UHFFFAOYSA-N 0.000 claims description 2
JYKWGYSWFNOFJB-UHFFFAOYSA-N 1'-[[6-(dimethylamino)pyridin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN(C)C1=CC=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=N1 JYKWGYSWFNOFJB-UHFFFAOYSA-N 0.000 claims description 2
HZHXWERULSIVTR-UHFFFAOYSA-N 1'-[[6-(dimethylamino)pyridin-3-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=NC(N(C)C)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O HZHXWERULSIVTR-UHFFFAOYSA-N 0.000 claims description 2
CKXAXBVNVMYOCA-UHFFFAOYSA-N 1'-[[6-(trifluoromethyl)pyridin-2-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound FC(F)(F)C1=CC=CC(CN2C3=CC=CC=C3C3(C4=CC=5OCCOC=5C=C4OC3)C2=O)=N1 CKXAXBVNVMYOCA-UHFFFAOYSA-N 0.000 claims description 2
KGEMRHAINGERNN-UHFFFAOYSA-N 1'-[[6-(trifluoromethyl)pyridin-3-yl]methyl]spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=NC(C(F)(F)F)=CC=C1CN1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O KGEMRHAINGERNN-UHFFFAOYSA-N 0.000 claims description 2
VKGUVSAYGSOULK-UHFFFAOYSA-N 1'-benzhydryl-4',6'-dimethoxyspiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound O=C1C2(C3=CC=4OCCOC=4C=C3OC2)C=2C(OC)=CC(OC)=CC=2N1C(C=1C=CC=CC=1)C1=CC=CC=C1 VKGUVSAYGSOULK-UHFFFAOYSA-N 0.000 claims description 2
GYUGTGACHGLICF-UHFFFAOYSA-N 1'-benzhydryl-4'-(4-phenoxyphenyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC(C=3C=CC(OC=4C=CC=CC=4)=CC=3)=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 GYUGTGACHGLICF-UHFFFAOYSA-N 0.000 claims description 2
RIMIJFZYXWWQKU-UHFFFAOYSA-N 1'-benzhydryl-4'-quinolin-3-ylspiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC(C=3C=C4C=CC=CC4=NC=3)=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 RIMIJFZYXWWQKU-UHFFFAOYSA-N 0.000 claims description 2
GALHTLJOBUJWJQ-UHFFFAOYSA-N 1'-benzhydrylspiro[2,5,6,7-tetrahydrofuro[3,2-g]chromene-3,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4CCCOC=4C=C3OC2)C(=O)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 GALHTLJOBUJWJQ-UHFFFAOYSA-N 0.000 claims description 2
VZAYEYVKFJJUGH-UHFFFAOYSA-N 1'-cyclopropylspiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C12=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C(=O)N1C1CC1 VZAYEYVKFJJUGH-UHFFFAOYSA-N 0.000 claims description 2
MQRVSVIVKDRIMI-UHFFFAOYSA-N 1'-methyl-2'-oxo-n-(pyridin-2-ylmethyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-4'-carboxamide Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2C(=O)NCC1=CC=CC=N1 MQRVSVIVKDRIMI-UHFFFAOYSA-N 0.000 claims description 2
JAGMZXJWIGEXLV-UHFFFAOYSA-N 1'-methyl-2'-oxo-n-pentylspiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-4'-carboxamide Chemical compound O1CCOC(C=C23)=C1C=C3OCC21C(=O)N(C)C2=C1C(C(=O)NCCCCC)=CC=C2 JAGMZXJWIGEXLV-UHFFFAOYSA-N 0.000 claims description 2
NJKBBDSLUMLJHJ-UHFFFAOYSA-N 1'-methyl-2'-oxospiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-4'-carbonitrile Chemical compound C1=CC=C(C#N)C2=C1N(C)C(=O)C21C2=CC(OCCO3)=C3C=C2OC1 NJKBBDSLUMLJHJ-UHFFFAOYSA-N 0.000 claims description 2
OZHJQVGIEZNSBH-UHFFFAOYSA-N 1'-methyl-2'-oxospiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-4'-carboxamide Chemical compound C1=CC=C(C(N)=O)C2=C1N(C)C(=O)C21C2=CC(OCCO3)=C3C=C2OC1 OZHJQVGIEZNSBH-UHFFFAOYSA-N 0.000 claims description 2
ZIJGYBNOOUKQLX-UHFFFAOYSA-N 1'-methyl-2'-oxospiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-4'-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=C1N(C)C(=O)C21C2=CC(OCCO3)=C3C=C2OC1 ZIJGYBNOOUKQLX-UHFFFAOYSA-N 0.000 claims description 2
VBSRDSJYNYXUPB-UHFFFAOYSA-N 1'-methyl-4'-(1-methylpyrazol-4-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2C=1C=NN(C)C=1 VBSRDSJYNYXUPB-UHFFFAOYSA-N 0.000 claims description 2
WQGZRGLQNFSATD-UHFFFAOYSA-N 1'-methyl-4'-(1h-pyrazol-4-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2C=1C=NNC=1 WQGZRGLQNFSATD-UHFFFAOYSA-N 0.000 claims description 2
BRCHHUUOUFWWJM-UHFFFAOYSA-N 1'-methyl-4'-(1h-pyrazol-5-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2C=1C=CNN=1 BRCHHUUOUFWWJM-UHFFFAOYSA-N 0.000 claims description 2
GKUOUFUQJDZTGJ-UHFFFAOYSA-N 1'-methyl-4'-(2-methyl-1,3-thiazol-4-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2C1=CSC(C)=N1 GKUOUFUQJDZTGJ-UHFFFAOYSA-N 0.000 claims description 2
VEZTVLUCTUHDOY-UHFFFAOYSA-N 1'-methyl-4'-(2-oxochromen-7-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound C1=CC(=O)OC2=CC(C3=CC=CC4=C3C3(C5=CC=6OCCOC=6C=C5OC3)C(=O)N4C)=CC=C21 VEZTVLUCTUHDOY-UHFFFAOYSA-N 0.000 claims description 2
ZGLOFOSPORMKJX-UHFFFAOYSA-N 1'-methyl-4'-(2-oxopyridin-1-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2N1C=CC=CC1=O ZGLOFOSPORMKJX-UHFFFAOYSA-N 0.000 claims description 2
GCCOWDMTXIQEFW-UHFFFAOYSA-N 1'-methyl-4'-(2-oxopyrrolidin-1-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2N1CCCC1=O GCCOWDMTXIQEFW-UHFFFAOYSA-N 0.000 claims description 2
QTUHYQVXSXEZNP-UHFFFAOYSA-N 1'-methyl-4'-(3-morpholin-4-ylphenoxy)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2OC(C=1)=CC=CC=1N1CCOCC1 QTUHYQVXSXEZNP-UHFFFAOYSA-N 0.000 claims description 2
YLJJWFRBQLPDRZ-UHFFFAOYSA-N 1'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2C1=NOC(C)=N1 YLJJWFRBQLPDRZ-UHFFFAOYSA-N 0.000 claims description 2
PPQVFXQSJHILGM-UHFFFAOYSA-N 1'-methyl-4'-(5-oxo-1,2-dihydropyrazol-3-yl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2C=1C=C(O)NN=1 PPQVFXQSJHILGM-UHFFFAOYSA-N 0.000 claims description 2
VIRCMSOLOCANNV-UHFFFAOYSA-N 1'-methyl-4'-(pyrrolidine-1-carbonyl)spiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2C(=O)N1CCCC1 VIRCMSOLOCANNV-UHFFFAOYSA-N 0.000 claims description 2
IUXOXATWJNHHMJ-UHFFFAOYSA-N 1'-methyl-4'-[3-(trifluoromethyl)pyridin-2-yl]oxyspiro[3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine-8,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCCOC=4C=C3OC2)C2=C1C=CC=C2OC1=NC=CC=C1C(F)(F)F IUXOXATWJNHHMJ-UHFFFAOYSA-N 0.000 claims description 2
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XPUFNEFIQRLRLK-QGZVFWFLSA-N (3r)-6'-methoxy-5'-methylspiro[1h-indole-3,3'-2h-1-benzofuran]-2-one Chemical compound O=C1NC2=CC=CC=C2[C@]21COC1=C2C=C(C)C(OC)=C1 XPUFNEFIQRLRLK-QGZVFWFLSA-N 0.000 description 1
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MCLDQIWDLILQOP-HXUWFJFHSA-N (3s)-4-(furan-3-yl)spiro[1h-indole-3,7'-6h-furo[2,3-f][1,3]benzodioxole]-2-one Chemical compound O=C([C@]1(C2=CC=3OCOC=3C=C2OC1)C1=2)NC1=CC=CC=2C=1C=COC=1 MCLDQIWDLILQOP-HXUWFJFHSA-N 0.000 description 1
XPUFNEFIQRLRLK-KRWDZBQOSA-N (3s)-6'-methoxy-5'-methylspiro[1h-indole-3,3'-2h-1-benzofuran]-2-one Chemical compound O=C1NC2=CC=CC=C2[C@@]21COC1=C2C=C(C)C(OC)=C1 XPUFNEFIQRLRLK-KRWDZBQOSA-N 0.000 description 1
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RWJHBUZYMGZNLW-UHFFFAOYSA-N 1'-methyl-4'-(oxolan-3-yl)spiro[6h-furo[2,3-f][1,3]benzodioxole-7,3'-indole]-2'-one Chemical compound CN1C(=O)C2(C3=CC=4OCOC=4C=C3OC2)C2=C1C=CC=C2C1CCOC1 RWJHBUZYMGZNLW-UHFFFAOYSA-N 0.000 description 1
PDMGPGZJCMVLTK-UHFFFAOYSA-N 1'-methylspiro[1h-indole-3,7'-6h-furo[3,2-f][1,3]benzoxazole]-2,2'-dione Chemical compound O=C1NC2=CC=CC=C2C21COC1=C2C=C2N(C)C(=O)OC2=C1 PDMGPGZJCMVLTK-UHFFFAOYSA-N 0.000 description 1
LIAOTGPDEKPOAT-UHFFFAOYSA-N 1'-methylspiro[1h-indole-3,8'-7h-furo[3,2-g][1,4]benzoxazine]-2,2'-dione Chemical compound O=C1NC2=CC=CC=C2C21COC1=C2C=C2N(C)C(=O)COC2=C1 LIAOTGPDEKPOAT-UHFFFAOYSA-N 0.000 description 1
125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
YCQIBRJQQSITME-UHFFFAOYSA-N 1-[[2-(fluoromethyl)phenyl]methyl]spiro[1h-indene-3,8'-3,7-dihydro-2h-furo[2,3-g][1,4]benzodioxine]-2-one Chemical compound FCC1=CC=CC=C1CC1C2=CC=CC=C2C2(C3=CC=4OCCOC=4C=C3OC2)C1=O YCQIBRJQQSITME-UHFFFAOYSA-N 0.000 description 1
VCBKUQZDTMWMAP-YXZNYDIRSA-N 1-methyl-1'-[[(2r)-oxolan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[3,2-g][1,4]benzoxazine-8,3'-indole]-2'-one;hydrochloride Chemical compound Cl.C1=2C=C3N(C)CCOC3=CC=2OCC1(C1=CC=CC=C11)C(=O)N1C[C@H]1CCCO1 VCBKUQZDTMWMAP-YXZNYDIRSA-N 0.000 description 1
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BOFKPDBDUVYSKT-UHFFFAOYSA-N 1-methyl-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[3,7-dihydro-2h-furo[3,2-g][1,4]benzoxazine-8,3'-indole]-2'-one;hydrochloride Chemical compound Cl.C1=2C=C3N(C)CCOC3=CC=2OCC1(C1=CC=CC=C11)C(=O)N1CC1=CC=C(C(F)(F)F)O1 BOFKPDBDUVYSKT-UHFFFAOYSA-N 0.000 description 1
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125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
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JP2011532189A 2008-10-17 2009-10-13 治療剤としてのスピロオキシインドール化合物およびそれらの使用 Expired - Fee Related JP5554337B2 (ja)