JP2013515033A - オレキシン受容体アンタゴニストとしてのジアザ−スピロ［５．５］ウンデカン類 - Google Patents

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Publication number

JP2013515033A

JP2013515033A JP2012545277A JP2012545277A JP2013515033A JP 2013515033 A JP2013515033 A JP 2013515033A JP 2012545277 A JP2012545277 A JP 2012545277A JP 2012545277 A JP2012545277 A JP 2012545277A JP 2013515033 A JP2013515033 A JP 2013515033A

Authority

JP

Japan

Prior art keywords

diazaspiro

undecan

methyl

quinoxalin

ring system

Prior art date

2009-12-21

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• 229940123730 Orexin receptor antagonist Drugs 0.000 title description 5
• XCRMJVAKOKRMRS-UHFFFAOYSA-N 1,2-diazaspiro[5.5]undecane Chemical class C1CCCCC21NNCCC2 XCRMJVAKOKRMRS-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 319
• 239000003814 drug Substances 0.000 claims abstract description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 329
• 125000004122 cyclic group Chemical group 0.000 claims description 236
• 229910052736 halogen Inorganic materials 0.000 claims description 226
• 150000002367 halogens Chemical class 0.000 claims description 225
• 229910052757 nitrogen Inorganic materials 0.000 claims description 222
• 125000000217 alkyl group Chemical group 0.000 claims description 172
• 125000003118 aryl group Chemical group 0.000 claims description 140
• 125000001424 substituent group Chemical group 0.000 claims description 124
• 125000001188 haloalkyl group Chemical group 0.000 claims description 116
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 109
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 109
• 125000005842 heteroatom Chemical group 0.000 claims description 109
• 229910052760 oxygen Inorganic materials 0.000 claims description 109
• 239000001301 oxygen Chemical group 0.000 claims description 109
• 229910052717 sulfur Chemical group 0.000 claims description 109
• 239000011593 sulfur Chemical group 0.000 claims description 109
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 106
• 125000000623 heterocyclic group Chemical group 0.000 claims description 102
• 125000003545 alkoxy group Chemical group 0.000 claims description 95
• -1 benzo [d] isoxazol-3-ylmethyl Chemical group 0.000 claims description 87
• 238000000034 method Methods 0.000 claims description 84
• 125000002950 monocyclic group Chemical group 0.000 claims description 83
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 82
• 125000004434 sulfur atom Chemical group 0.000 claims description 82
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 81
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 71
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
• 150000003839 salts Chemical group 0.000 claims description 43
• 229920006395 saturated elastomer Polymers 0.000 claims description 42
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 41
• 208000035475 disorder Diseases 0.000 claims description 36
• 125000006413 ring segment Chemical group 0.000 claims description 34
• 125000002619 bicyclic group Chemical group 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 33
• 108050000742 Orexin Receptor Proteins 0.000 claims description 26
• 102000008834 Orexin receptor Human genes 0.000 claims description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 208000011117 substance-related disease Diseases 0.000 claims description 17
• 208000019116 sleep disease Diseases 0.000 claims description 16
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 14
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 14
• 208000030814 Eating disease Diseases 0.000 claims description 13
• 235000014632 disordered eating Nutrition 0.000 claims description 13
• 208000024827 Alzheimer disease Diseases 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000005605 benzo group Chemical group 0.000 claims description 10
• 125000003367 polycyclic group Chemical group 0.000 claims description 10
• 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 9
• MPJDJGUFVOTTDY-UHFFFAOYSA-N 1-(1h-indol-4-ylmethyl)-9-quinoxalin-2-yl-1,9-diazaspiro[5.5]undecan-2-one Chemical compound O=C1CCCC2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)N1CC1=CC=CC2=C1C=CN2 MPJDJGUFVOTTDY-UHFFFAOYSA-N 0.000 claims description 8
• VPARAVFFNOQZEG-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5NC=3)C4=O)=CN=C21 VPARAVFFNOQZEG-UHFFFAOYSA-N 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 7
• OBJJCTFQGWCXGH-UHFFFAOYSA-N 1-(1h-indol-3-ylmethyl)-9-quinoxalin-2-yl-1,9-diazaspiro[5.5]undecan-2-one Chemical compound C1=CC=C2C(CN3C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCCC3=O)=CNC2=C1 OBJJCTFQGWCXGH-UHFFFAOYSA-N 0.000 claims description 7
• XOEYXHCZYQOOHV-UHFFFAOYSA-N 1-[(2,5-dimethylphenyl)methyl]-9-quinoxalin-2-yl-1,9-diazaspiro[5.5]undecan-2-one Chemical compound CC1=CC=C(C)C(CN2C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCCC2=O)=C1 XOEYXHCZYQOOHV-UHFFFAOYSA-N 0.000 claims description 7
• VIOJTUUTJMPSRP-UHFFFAOYSA-N 2-(naphthalen-1-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5C=CC=3)C4=O)=CN=C21 VIOJTUUTJMPSRP-UHFFFAOYSA-N 0.000 claims description 7
• MKVTWIQITPVFGY-UHFFFAOYSA-N 2-[(2-bromopyridin-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=NC(Br)=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 MKVTWIQITPVFGY-UHFFFAOYSA-N 0.000 claims description 7
• UXTQDECOFADUAA-UHFFFAOYSA-N 9-(1,3-benzoxazol-2-yl)-1-(1h-indol-4-ylmethyl)-1,9-diazaspiro[5.5]undecan-2-one Chemical compound O=C1CCCC2(CCN(CC2)C=2OC3=CC=CC=C3N=2)N1CC1=CC=CC2=C1C=CN2 UXTQDECOFADUAA-UHFFFAOYSA-N 0.000 claims description 7
• QKSFTCQNZKTOMM-UHFFFAOYSA-N 9-(1,3-benzoxazol-2-yl)-2-(1h-indol-3-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2OC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5NC=3)C4=O)=NC2=C1 QKSFTCQNZKTOMM-UHFFFAOYSA-N 0.000 claims description 7
• JGQMNLQDUUXCLD-UHFFFAOYSA-N 9-(1h-benzimidazol-2-yl)-2-benzyl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1CCC2(CCN(CC2)C=2NC3=CC=CC=C3N=2)C(=O)N1CC1=CC=CC=C1 JGQMNLQDUUXCLD-UHFFFAOYSA-N 0.000 claims description 7
• UQDZEOCEKHULPR-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[[2-(triazol-2-yl)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1CCC2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)C(=O)N1CC1=CC=CC=C1N1N=CC=N1 UQDZEOCEKHULPR-UHFFFAOYSA-N 0.000 claims description 7
• XVGFXAQGBMEMLN-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[[3-(triazol-1-yl)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1CCC2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)C(=O)N1CC(C=1)=CC=CC=1N1C=CN=N1 XVGFXAQGBMEMLN-UHFFFAOYSA-N 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• 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 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
• ITYCFGYDQTYTHU-UHFFFAOYSA-N 1-[(1-methylindol-4-yl)methyl]-9-quinoxalin-2-yl-1,9-diazaspiro[5.5]undecan-2-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCC(=O)N4CC3=C4C=CN(C4=CC=C3)C)=CN=C21 ITYCFGYDQTYTHU-UHFFFAOYSA-N 0.000 claims description 6
• FAHIANPLXOTJJI-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-quinolin-3-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=CC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5NC=3)C4=O)=CN=C21 FAHIANPLXOTJJI-UHFFFAOYSA-N 0.000 claims description 6
• DCKAOKXRHCMSPN-UHFFFAOYSA-N 2-(1h-indol-4-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C=5C=CNC=5C=CC=3)C4=O)=CN=C21 DCKAOKXRHCMSPN-UHFFFAOYSA-N 0.000 claims description 6
• IPMCDCHOUVXMRQ-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-5-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C=5OCCOC=5C=CC=3)C4=O)=CN=C21 IPMCDCHOUVXMRQ-UHFFFAOYSA-N 0.000 claims description 6
• DOJGKKMFFVBILG-UHFFFAOYSA-N 2-[(2-methoxypyridin-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=NC(OC)=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 DOJGKKMFFVBILG-UHFFFAOYSA-N 0.000 claims description 6
• CWYFTFBSOGXBMH-UHFFFAOYSA-N 2-[(3-pyridin-3-ylphenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1CCC2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)C(=O)N1CC(C=1)=CC=CC=1C1=CC=CN=C1 CWYFTFBSOGXBMH-UHFFFAOYSA-N 0.000 claims description 6
• IVZNDXLYJSZKHL-UHFFFAOYSA-N 2-[[2-(1-methylpyrazol-4-yl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=NN(C)C=C1C1=CC=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 IVZNDXLYJSZKHL-UHFFFAOYSA-N 0.000 claims description 6
• ORQIXYIDXFFJOU-UHFFFAOYSA-N 2-[[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=NOC(C=2C(=CC=CC=2)CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=N1 ORQIXYIDXFFJOU-UHFFFAOYSA-N 0.000 claims description 6
• JZIQDXKUSQEYLS-UHFFFAOYSA-N 2-benzyl-9-(1-methylbenzimidazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound N=1C2=CC=CC=C2N(C)C=1N(CC1)CCC1(C1=O)CCCN1CC1=CC=CC=C1 JZIQDXKUSQEYLS-UHFFFAOYSA-N 0.000 claims description 6
• UDEVJXZAPAEOER-UHFFFAOYSA-N 9-(1,3-benzothiazol-2-yl)-2-(1h-indol-3-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2SC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5NC=3)C4=O)=NC2=C1 UDEVJXZAPAEOER-UHFFFAOYSA-N 0.000 claims description 6
• RBIXHGMLCUCQHS-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[[3-(triazol-2-yl)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1CCC2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)C(=O)N1CC(C=1)=CC=CC=1N1N=CC=N1 RBIXHGMLCUCQHS-UHFFFAOYSA-N 0.000 claims description 6
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
• CZLPVSPUVXAEBF-UHFFFAOYSA-N 1-(1,2-benzoxazol-3-ylmethyl)-9-quinoxalin-2-yl-1,9-diazaspiro[5.5]undecan-2-one Chemical compound C1=CC=C2C(CN3C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCCC3=O)=NOC2=C1 CZLPVSPUVXAEBF-UHFFFAOYSA-N 0.000 claims description 5
• KCMMYXVXOINAMH-UHFFFAOYSA-N 1-(1h-indol-4-ylmethyl)-9-(5-methyl-1,3-benzoxazol-2-yl)-1,9-diazaspiro[5.5]undecan-2-one Chemical compound N=1C2=CC(C)=CC=C2OC=1N(CC1)CCC21CCCC(=O)N2CC1=CC=CC2=C1C=CN2 KCMMYXVXOINAMH-UHFFFAOYSA-N 0.000 claims description 5
• JLTNLZCXGDESDF-UHFFFAOYSA-N 1-(1h-indol-4-ylmethyl)-9-(5-phenyl-1,3,4-oxadiazol-2-yl)-1,9-diazaspiro[5.5]undecan-2-one Chemical compound C=1C=CC=2NC=CC=2C=1CN1C(=O)CCCC1(CC1)CCN1C(O1)=NN=C1C1=CC=CC=C1 JLTNLZCXGDESDF-UHFFFAOYSA-N 0.000 claims description 5
• QDAZWKJDVZIOTR-UHFFFAOYSA-N 1-[(1-methylpyrrolo[2,3-b]pyridin-3-yl)methyl]-9-quinoxalin-2-yl-1,9-diazaspiro[5.5]undecan-2-one Chemical compound C12=CC=CN=C2N(C)C=C1CN1C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCCC1=O QDAZWKJDVZIOTR-UHFFFAOYSA-N 0.000 claims description 5
• OYVQUEIDYQCADD-UHFFFAOYSA-N 1-benzyl-9-quinoxalin-2-yl-1,9-diazaspiro[5.5]undecan-2-one Chemical compound O=C1CCCC2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)N1CC1=CC=CC=C1 OYVQUEIDYQCADD-UHFFFAOYSA-N 0.000 claims description 5
• KJCKVHGVQQWMCK-UHFFFAOYSA-N 2-(1,3-benzodioxol-4-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C=5OCOC=5C=CC=3)C4=O)=CN=C21 KJCKVHGVQQWMCK-UHFFFAOYSA-N 0.000 claims description 5
• ONVQIMRWQOAOKB-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C=C5OCOC5=CC=3)C4=O)=CN=C21 ONVQIMRWQOAOKB-UHFFFAOYSA-N 0.000 claims description 5
• KGQXSIZDLQNUJM-UHFFFAOYSA-N 2-(1h-indol-2-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3NC5=CC=CC=C5C=3)C4=O)=CN=C21 KGQXSIZDLQNUJM-UHFFFAOYSA-N 0.000 claims description 5
• ASVFNNOBBUVMDZ-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(3-methylquinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(CN3CCCC4(CCN(CC4)C4=NC5=CC=CC=C5N=C4C)C3=O)=CNC2=C1 ASVFNNOBBUVMDZ-UHFFFAOYSA-N 0.000 claims description 5
• MYAZPXNTYKPWOO-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(4-methyl-6-pyrazol-1-ylpyrimidin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound N=1C(N2CCC3(C(N(CC=4C5=CC=CC=C5NC=4)CCC3)=O)CC2)=NC(C)=CC=1N1C=CC=N1 MYAZPXNTYKPWOO-UHFFFAOYSA-N 0.000 claims description 5
• LHBMNHBCDMSAEI-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(4-methylphthalazin-1-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C12=CC=CC=C2C(C)=NN=C1N1CCC2(C(N(CC=3C4=CC=CC=C4NC=3)CCC2)=O)CC1 LHBMNHBCDMSAEI-UHFFFAOYSA-N 0.000 claims description 5
• DDYKRFYMWLKLMC-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(4-methylquinolin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(CN3CCCC4(CCN(CC4)C=4C=C(C5=CC=CC=C5N=4)C)C3=O)=CNC2=C1 DDYKRFYMWLKLMC-UHFFFAOYSA-N 0.000 claims description 5
• BRXQGNPEHXFBHX-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(4-phenylpyrimidin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1N(CC=2C3=CC=CC=C3NC=2)CCCC1(CC1)CCN1C(N=1)=NC=CC=1C1=CC=CC=C1 BRXQGNPEHXFBHX-UHFFFAOYSA-N 0.000 claims description 5
• WRTJGWPIGKTFGJ-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(4-pyridin-4-ylpyrimidin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1N(CC=2C3=CC=CC=C3NC=2)CCCC1(CC1)CCN1C(N=1)=NC=CC=1C1=CC=NC=C1 WRTJGWPIGKTFGJ-UHFFFAOYSA-N 0.000 claims description 5
• CUTTZCUELYNFNU-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(5-phenyl-1,3,4-thiadiazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1N(CC=2C3=CC=CC=C3NC=2)CCCC1(CC1)CCN1C(S1)=NN=C1C1=CC=CC=C1 CUTTZCUELYNFNU-UHFFFAOYSA-N 0.000 claims description 5
• VWNWGZFSBMMYSN-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(6-methoxy-1h-benzimidazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(CN3CCCC4(CCN(CC4)C=4NC5=CC=C(C=C5N=4)OC)C3=O)=CNC2=C1 VWNWGZFSBMMYSN-UHFFFAOYSA-N 0.000 claims description 5
• VQEHPNSRQISWKA-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(6-methyl-1,3-benzothiazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(CN3CCCC4(CCN(CC4)C4=NC5=CC=C(C=C5S4)C)C3=O)=CNC2=C1 VQEHPNSRQISWKA-UHFFFAOYSA-N 0.000 claims description 5
• MDFKGRCORWAMOB-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(6-methyl-1h-benzimidazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(CN3CCCC4(CCN(CC4)C=4NC5=CC=C(C=C5N=4)C)C3=O)=CNC2=C1 MDFKGRCORWAMOB-UHFFFAOYSA-N 0.000 claims description 5
• MCFGOFCCAJILET-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(6-phenylpyrimidin-4-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1N(CC=2C3=CC=CC=C3NC=2)CCCC1(CC1)CCN1C(N=CN=1)=CC=1C1=CC=CC=C1 MCFGOFCCAJILET-UHFFFAOYSA-N 0.000 claims description 5
• VEADNGBANTZLOA-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1N(CC=2C3=CC=CC=C3NC=2)CCCC1(CC1)CCN1C1=NC=NC2=C1C=CN2 VEADNGBANTZLOA-UHFFFAOYSA-N 0.000 claims description 5
• RQJGDPJULJUSEZ-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-[5-(1,3-thiazol-2-yl)pyridin-2-yl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1N(CC=2C3=CC=CC=C3NC=2)CCCC1(CC1)CCN1C(N=C1)=CC=C1C1=NC=CS1 RQJGDPJULJUSEZ-UHFFFAOYSA-N 0.000 claims description 5
• YRSZHAQJGOPTOR-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-isoquinolin-1-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5NC=3)C4=O)=NC=CC2=C1 YRSZHAQJGOPTOR-UHFFFAOYSA-N 0.000 claims description 5
• CKIHTGXZLGORGW-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-pyrido[2,3-b]pyrazin-7-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound N1=CC=NC2=CC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5NC=3)C4=O)=CN=C21 CKIHTGXZLGORGW-UHFFFAOYSA-N 0.000 claims description 5
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