JP2013515033A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013515033A5 JP2013515033A5 JP2012545277A JP2012545277A JP2013515033A5 JP 2013515033 A5 JP2013515033 A5 JP 2013515033A5 JP 2012545277 A JP2012545277 A JP 2012545277A JP 2012545277 A JP2012545277 A JP 2012545277A JP 2013515033 A5 JP2013515033 A5 JP 2013515033A5
- Authority
- JP
- Japan
- Prior art keywords
- diazaspiro
- undecan
- quinoxalin
- methyl
- ring system
- Prior art date
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 benzo [d] isoxazol-3-ylmethyl Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 59
- 125000004122 cyclic group Chemical group 0.000 claims 45
- 229910052757 nitrogen Inorganic materials 0.000 claims 39
- 229910052736 halogen Inorganic materials 0.000 claims 37
- 150000002367 halogens Chemical class 0.000 claims 37
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000001424 substituent group Chemical group 0.000 claims 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 19
- 125000005842 heteroatom Chemical group 0.000 claims 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 19
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 239000001301 oxygen Chemical group 0.000 claims 19
- 229910052717 sulfur Chemical group 0.000 claims 19
- 239000011593 sulfur Chemical group 0.000 claims 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims 18
- 125000004434 sulfur atom Chemical group 0.000 claims 18
- 125000001188 haloalkyl group Chemical group 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 125000002950 monocyclic group Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000006413 ring segment Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 3
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 3
- 150000003839 salts Chemical group 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000003367 polycyclic group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- IIRZDIJXZSOZKI-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-(4-pyrazol-1-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=1N1C=CC=N1 IIRZDIJXZSOZKI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- AIDAWRFKCJZKLP-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-pyrido[3,4-b]pyrazin-7-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CN=C2C=NC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5NC=3)C4=O)=CC2=N1 AIDAWRFKCJZKLP-UHFFFAOYSA-N 0.000 claims 1
- RSXGQEFCZXHYTD-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-quinazolin-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)=NC=C21 RSXGQEFCZXHYTD-UHFFFAOYSA-N 0.000 claims 1
- KZAXTADHTDIFNK-UHFFFAOYSA-N 2-(1h-indol-3-ylmethyl)-9-quinolin-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)=CC=C21 KZAXTADHTDIFNK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- XFNFZPYARVVKPM-UHFFFAOYSA-N 2-(1h-indol-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=C5C=CNC5=CC=3)C4=O)=CN=C21 XFNFZPYARVVKPM-UHFFFAOYSA-N 0.000 claims 1
- PLYROBNEDAWALN-UHFFFAOYSA-N 2-(1h-pyrrolo[2,3-b]pyridin-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=CN=C5NC=3)C4=O)=CN=C21 PLYROBNEDAWALN-UHFFFAOYSA-N 0.000 claims 1
- QVYPQEYTLBZOID-UHFFFAOYSA-N 2-(2,1,3-benzothiadiazol-4-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C5=NSN=C5C=CC=3)C4=O)=CN=C21 QVYPQEYTLBZOID-UHFFFAOYSA-N 0.000 claims 1
- ONMLEQWOUFEECV-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-5-ylmethyl)-9-furo[3,2-c]pyridin-4-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1N(CC=2C=3OCCOC=3C=CC=2)CCCC1(CC1)CCN1C1=NC=CC2=C1C=CO2 ONMLEQWOUFEECV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SHTZMNFYPOZYOQ-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C=C5OCCOC5=CC=3)C4=O)=CN=C21 SHTZMNFYPOZYOQ-UHFFFAOYSA-N 0.000 claims 1
- ORKRWFNKKLIAJK-UHFFFAOYSA-N 2-(2,3-dihydro-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=5CCNC=5C=CC=3)C4=O)=CN=C21 ORKRWFNKKLIAJK-UHFFFAOYSA-N 0.000 claims 1
- YIIQTAIBOHMKKD-UHFFFAOYSA-N 2-(2h-indazol-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=C5NN=3)C4=O)=CN=C21 YIIQTAIBOHMKKD-UHFFFAOYSA-N 0.000 claims 1
- CQQJVWRJNOOJAU-UHFFFAOYSA-N 2-(3,4-dihydro-2h-1,4-benzoxazin-8-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C=5OCCNC=5C=CC=3)C4=O)=CN=C21 CQQJVWRJNOOJAU-UHFFFAOYSA-N 0.000 claims 1
- IKCOPTGWZOAHLH-UHFFFAOYSA-N 2-(benzotriazol-1-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CN3C5=CC=CC=C5N=N3)C4=O)=CN=C21 IKCOPTGWZOAHLH-UHFFFAOYSA-N 0.000 claims 1
- HQFDFSMMWMKLLO-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-3-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3N5C=CC=CC5=NC=3)C4=O)=CN=C21 HQFDFSMMWMKLLO-UHFFFAOYSA-N 0.000 claims 1
- RPVVAVOLOVQNCK-UHFFFAOYSA-N 2-(isoquinolin-5-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=NC=C5C=CC=3)C4=O)=CN=C21 RPVVAVOLOVQNCK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RGPJPIXAOXPJFM-UHFFFAOYSA-N 2-(naphthalen-2-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C=C5C=CC=CC5=CC=3)C4=O)=CN=C21 RGPJPIXAOXPJFM-UHFFFAOYSA-N 0.000 claims 1
- OPRRWPUDJZCZQJ-UHFFFAOYSA-N 2-(pyrazolo[1,5-a]pyridin-3-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC3=C5C=CC=CN5N=C3)C4=O)=CN=C21 OPRRWPUDJZCZQJ-UHFFFAOYSA-N 0.000 claims 1
- CAFVMNXQDPJEHB-UHFFFAOYSA-N 2-(pyridin-2-ylmethyl)-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)N1CC1=CC=CC=N1 CAFVMNXQDPJEHB-UHFFFAOYSA-N 0.000 claims 1
- ORBUGKQTLNFKCT-UHFFFAOYSA-N 2-(pyridin-3-ylmethyl)-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)N1CC1=CC=CN=C1 ORBUGKQTLNFKCT-UHFFFAOYSA-N 0.000 claims 1
- VPNFXQPUKXDCMX-UHFFFAOYSA-N 2-(pyridin-4-ylmethyl)-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)N1CC1=CC=NC=C1 VPNFXQPUKXDCMX-UHFFFAOYSA-N 0.000 claims 1
- JSRKOBGHJZTKOT-UHFFFAOYSA-N 2-(quinolin-8-ylmethyl)-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3C5=NC=CC=C5C=CC=3)C4=O)=CN=C21 JSRKOBGHJZTKOT-UHFFFAOYSA-N 0.000 claims 1
- OPMZLOVNFKDPSQ-UHFFFAOYSA-N 2-[(1,5-dimethylpyrazol-3-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CN1C(C)=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=N1 OPMZLOVNFKDPSQ-UHFFFAOYSA-N 0.000 claims 1
- CKAGIKJBFWRZRK-UHFFFAOYSA-N 2-[(1-benzylimidazol-2-yl)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)N1CC1=NC=CN1CC1=CC=CC=C1 CKAGIKJBFWRZRK-UHFFFAOYSA-N 0.000 claims 1
- VQUVXWJFJDRZTJ-UHFFFAOYSA-N 2-[(1-methyl-2,3-dihydroindol-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CCCN(C4=O)CC4=CC=CC5=C4CCN5C)CC3)=CN=C21 VQUVXWJFJDRZTJ-UHFFFAOYSA-N 0.000 claims 1
- PKWXTQKEFBRDDG-UHFFFAOYSA-N 2-[(1-methylbenzimidazol-2-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2N(C)C(CN3C(C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCC3)=O)=NC2=C1 PKWXTQKEFBRDDG-UHFFFAOYSA-N 0.000 claims 1
- IYYQALRAHAPOFJ-UHFFFAOYSA-N 2-[(1-methylindazol-3-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C12=CC=CC=C2N(C)N=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 IYYQALRAHAPOFJ-UHFFFAOYSA-N 0.000 claims 1
- UPYACEDVQZFZPK-UHFFFAOYSA-N 2-[(1-methylindazol-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CCCN(C4=O)CC4=C5C=NN(C5=CC=C4)C)CC3)=CN=C21 UPYACEDVQZFZPK-UHFFFAOYSA-N 0.000 claims 1
- NEMITPZPAUHBCI-UHFFFAOYSA-N 2-[(1-methylindol-3-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C12=CC=CC=C2N(C)C=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 NEMITPZPAUHBCI-UHFFFAOYSA-N 0.000 claims 1
- UAJUSLHTLYNZMU-UHFFFAOYSA-N 2-[(1-methylindol-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CCCN(C4=O)CC4=C5C=CN(C5=CC=C4)C)CC3)=CN=C21 UAJUSLHTLYNZMU-UHFFFAOYSA-N 0.000 claims 1
- WYFKPDXFQZCLPZ-UHFFFAOYSA-N 2-[(1-phenyltetrazol-5-yl)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)N1CC1=NN=NN1C1=CC=CC=C1 WYFKPDXFQZCLPZ-UHFFFAOYSA-N 0.000 claims 1
- CHOSDPFKVBBAJD-UHFFFAOYSA-N 2-[(2,3-dimethoxyphenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound COC1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1OC CHOSDPFKVBBAJD-UHFFFAOYSA-N 0.000 claims 1
- ZNFONBUCVIDRIG-UHFFFAOYSA-N 2-[(2,3-dimethylphenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1C ZNFONBUCVIDRIG-UHFFFAOYSA-N 0.000 claims 1
- QOAKHLCNBPPPDU-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=CC=C(C)C(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 QOAKHLCNBPPPDU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YMDLKPYRQYKYGV-UHFFFAOYSA-N 2-[(2-fluoro-3-methoxyphenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound COC1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1F YMDLKPYRQYKYGV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FOIQMTJLYXDMJG-UHFFFAOYSA-N 2-[(2-methyl-1h-indol-3-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CCCN(C4=O)CC=4C5=CC=CC=C5NC=4C)CC3)=CN=C21 FOIQMTJLYXDMJG-UHFFFAOYSA-N 0.000 claims 1
- SKLKXAKXZQKETK-UHFFFAOYSA-N 2-[(2-methyl-1h-indol-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CCCN(C4=O)CC4=C5C=C(NC5=CC=C4)C)CC3)=CN=C21 SKLKXAKXZQKETK-UHFFFAOYSA-N 0.000 claims 1
- IWZSLLMIQLHQLK-UHFFFAOYSA-N 2-[(2-methylimidazo[1,2-a]pyridin-3-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CCCN(C4=O)CC=4N5C=CC=CC5=NC=4C)CC3)=CN=C21 IWZSLLMIQLHQLK-UHFFFAOYSA-N 0.000 claims 1
- FKDBADPVIQHCJX-UHFFFAOYSA-N 2-[(2-methylindazol-3-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CCCN(C4=O)CC4=C5C=CC=CC5=NN4C)CC3)=CN=C21 FKDBADPVIQHCJX-UHFFFAOYSA-N 0.000 claims 1
- COSQMAQWPCHUOS-UHFFFAOYSA-N 2-[(2-methylphenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=CC=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 COSQMAQWPCHUOS-UHFFFAOYSA-N 0.000 claims 1
- NRCOGRPQXQXDKP-UHFFFAOYSA-N 2-[(2-methylpyridin-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=NC(C)=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 NRCOGRPQXQXDKP-UHFFFAOYSA-N 0.000 claims 1
- NDITZTQINKQMSZ-UHFFFAOYSA-N 2-[(2-methylquinolin-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(C)=CC(CN3C(C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCC3)=O)=C21 NDITZTQINKQMSZ-UHFFFAOYSA-N 0.000 claims 1
- STTVZTQRVDUOOY-UHFFFAOYSA-N 2-[(2-morpholin-4-ylpyridin-4-yl)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=NC=1N1CCOCC1 STTVZTQRVDUOOY-UHFFFAOYSA-N 0.000 claims 1
- MICVVFLJIUYIBY-UHFFFAOYSA-N 2-[(2-oxo-1h-quinolin-4-yl)methyl]-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(=O)C=3)C4=O)=CN=C21 MICVVFLJIUYIBY-UHFFFAOYSA-N 0.000 claims 1
- UQYIQNCOOJDWHN-UHFFFAOYSA-N 2-[(2-pyrazol-1-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)N1CC1=CC=CC=C1N1C=CC=N1 UQYIQNCOOJDWHN-UHFFFAOYSA-N 0.000 claims 1
- JTBPCXHLACNRFP-UHFFFAOYSA-N 2-[(2-pyrazol-1-ylpyridin-4-yl)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=NC=1N1C=CC=N1 JTBPCXHLACNRFP-UHFFFAOYSA-N 0.000 claims 1
- DOLMGMPIYDNHPD-UHFFFAOYSA-N 2-[(2-pyrimidin-2-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)N1CC1=CC=CC=C1C1=NC=CC=N1 DOLMGMPIYDNHPD-UHFFFAOYSA-N 0.000 claims 1
- BTWNHCWHTULPOK-UHFFFAOYSA-N 2-[(3,4-dimethoxypyridin-2-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound COC1=CC=NC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1OC BTWNHCWHTULPOK-UHFFFAOYSA-N 0.000 claims 1
- PKROVAYILMETMR-UHFFFAOYSA-N 2-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=NOC(C)=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 PKROVAYILMETMR-UHFFFAOYSA-N 0.000 claims 1
- TWSRMFCCEFUHAK-UHFFFAOYSA-N 2-[(3,5-dimethylphenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=CC(C)=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 TWSRMFCCEFUHAK-UHFFFAOYSA-N 0.000 claims 1
- AXQVXRUOOIQUES-UHFFFAOYSA-N 2-[(3-benzylimidazol-4-yl)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)N1CC1=CN=CN1CC1=CC=CC=C1 AXQVXRUOOIQUES-UHFFFAOYSA-N 0.000 claims 1
- IKNJTXAWVYBBNQ-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]-9-(4-phenylpyrimidin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound ClC1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C(C=CN=3)C=3C=CC=CC=3)CCC2)=O)=C1 IKNJTXAWVYBBNQ-UHFFFAOYSA-N 0.000 claims 1
- CPQDJVJPRAAAAO-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound ClC1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 CPQDJVJPRAAAAO-UHFFFAOYSA-N 0.000 claims 1
- BLHRBZBPFNAVLB-UHFFFAOYSA-N 2-[(3-methyl-1,2-oxazol-5-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O1N=C(C)C=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 BLHRBZBPFNAVLB-UHFFFAOYSA-N 0.000 claims 1
- ZBFUYUUMMRIKBT-UHFFFAOYSA-N 2-[(3-methyl-5-phenyl-1,2-oxazol-4-yl)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=1C(C)=NOC=1C1=CC=CC=C1 ZBFUYUUMMRIKBT-UHFFFAOYSA-N 0.000 claims 1
- JVQBNXYNNZDXQF-UHFFFAOYSA-N 2-[(3-methylphenyl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 JVQBNXYNNZDXQF-UHFFFAOYSA-N 0.000 claims 1
- IUUPFHGCJUXVRC-UHFFFAOYSA-N 2-[(3-morpholin-4-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=1N1CCOCC1 IUUPFHGCJUXVRC-UHFFFAOYSA-N 0.000 claims 1
- HZWBBUMQVBEVRQ-UHFFFAOYSA-N 2-[(3-phenylimidazol-4-yl)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)N1CC1=CN=CN1C1=CC=CC=C1 HZWBBUMQVBEVRQ-UHFFFAOYSA-N 0.000 claims 1
- DHBHYLLJTLRILL-UHFFFAOYSA-N 2-[(3-phenylphenyl)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=CC=C1 DHBHYLLJTLRILL-UHFFFAOYSA-N 0.000 claims 1
- MANWMDXZWSBIHD-UHFFFAOYSA-N 2-[(3-pyrazin-2-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=CN=CC=N1 MANWMDXZWSBIHD-UHFFFAOYSA-N 0.000 claims 1
- MFNJDWIRSNXGEX-UHFFFAOYSA-N 2-[(3-pyrazol-1-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=1N1C=CC=N1 MFNJDWIRSNXGEX-UHFFFAOYSA-N 0.000 claims 1
- SZSBNPBHAYWCJQ-UHFFFAOYSA-N 2-[(3-pyridin-2-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=CC=N1 SZSBNPBHAYWCJQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VUJVFWIORLYYHR-UHFFFAOYSA-N 2-[(3-pyridin-4-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=NC=C1 VUJVFWIORLYYHR-UHFFFAOYSA-N 0.000 claims 1
- CWVRYJFYEUMVAB-UHFFFAOYSA-N 2-[(3-pyrimidin-2-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=NC=CC=N1 CWVRYJFYEUMVAB-UHFFFAOYSA-N 0.000 claims 1
- WMPZIOMESYYVBA-UHFFFAOYSA-N 2-[(3-pyrrol-1-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=1N1C=CC=C1 WMPZIOMESYYVBA-UHFFFAOYSA-N 0.000 claims 1
- RNLPJUPBLDTBNY-UHFFFAOYSA-N 2-[(4,6-dimethylpyridin-2-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=CC(C)=NC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 RNLPJUPBLDTBNY-UHFFFAOYSA-N 0.000 claims 1
- BPDQNYFRMUPQRT-UHFFFAOYSA-N 2-[(4-methyl-2,3-dihydro-1,4-benzoxazin-8-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CCCN(C4=O)CC4=C5OCCN(C5=CC=C4)C)CC3)=CN=C21 BPDQNYFRMUPQRT-UHFFFAOYSA-N 0.000 claims 1
- GBLJYPGPQWIJRB-UHFFFAOYSA-N 2-[(4-methyl-2-phenyl-1,3-oxazol-5-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O1C(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C(C)N=C1C1=CC=CC=C1 GBLJYPGPQWIJRB-UHFFFAOYSA-N 0.000 claims 1
- WQLGTLQORWJXLK-UHFFFAOYSA-N 2-[(4-pyrazol-1-ylpyridin-2-yl)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(N=CC=1)=CC=1N1C=CC=N1 WQLGTLQORWJXLK-UHFFFAOYSA-N 0.000 claims 1
- ZUIVALNMKCYBTN-UHFFFAOYSA-N 2-[(4-pyrimidin-2-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=C1)=CC=C1C1=NC=CC=N1 ZUIVALNMKCYBTN-UHFFFAOYSA-N 0.000 claims 1
- QRIJMXBWOATAPX-UHFFFAOYSA-N 2-[(5-cyclobutyl-1,2,4-oxadiazol-3-yl)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(N=1)=NOC=1C1CCC1 QRIJMXBWOATAPX-UHFFFAOYSA-N 0.000 claims 1
- XPVABYABKYPXHT-UHFFFAOYSA-N 2-[(5-methyl-1,2-oxazol-3-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O1C(C)=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=N1 XPVABYABKYPXHT-UHFFFAOYSA-N 0.000 claims 1
- WUXPKZJKAXKBRE-UHFFFAOYSA-N 2-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)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)N1CC1=C(C)ON=C1C1=CC=CC=C1 WUXPKZJKAXKBRE-UHFFFAOYSA-N 0.000 claims 1
- TYLLXOJRHHEOEX-UHFFFAOYSA-N 2-[(6-chloro-4h-1,3-benzodioxin-8-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O1COCC2=CC(Cl)=CC(CN3C(C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCC3)=O)=C21 TYLLXOJRHHEOEX-UHFFFAOYSA-N 0.000 claims 1
- OEBJOVXNWRUCLR-UHFFFAOYSA-N 2-[(6-chloropyridin-3-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=NC(Cl)=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 OEBJOVXNWRUCLR-UHFFFAOYSA-N 0.000 claims 1
- AANNPRMIRTUEMY-UHFFFAOYSA-N 2-[(6-fluoro-4h-1,3-benzodioxin-8-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O1COCC2=CC(F)=CC(CN3C(C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCC3)=O)=C21 AANNPRMIRTUEMY-UHFFFAOYSA-N 0.000 claims 1
- HMPZGWLJRHIBIW-UHFFFAOYSA-N 2-[(6-methylpyridin-2-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CC1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=N1 HMPZGWLJRHIBIW-UHFFFAOYSA-N 0.000 claims 1
- GDBCAXYOLOFJIR-UHFFFAOYSA-N 2-[(6-pyrazol-1-ylpyridin-2-yl)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(N=1)=CC=CC=1N1C=CC=N1 GDBCAXYOLOFJIR-UHFFFAOYSA-N 0.000 claims 1
- FJXBTRTZLXVHEH-UHFFFAOYSA-N 2-[(6-pyrrolidin-1-ylpyridin-2-yl)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(N=1)=CC=CC=1N1CCCC1 FJXBTRTZLXVHEH-UHFFFAOYSA-N 0.000 claims 1
- ZGQADBVTSAWJDD-UHFFFAOYSA-N 2-[1-(1h-indol-3-yl)ethyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(C(N3C(C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCC3)=O)C)=CNC2=C1 ZGQADBVTSAWJDD-UHFFFAOYSA-N 0.000 claims 1
- ZLBNDBYVURHRAL-UHFFFAOYSA-N 2-[[1-(2-methoxyphenyl)imidazol-2-yl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound COC1=CC=CC=C1N1C(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=NC=C1 ZLBNDBYVURHRAL-UHFFFAOYSA-N 0.000 claims 1
- DLWQIGJVBFVIJX-UHFFFAOYSA-N 2-[[2-(1,3-oxazol-2-yl)phenyl]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)N1CC1=CC=CC=C1C1=NC=CO1 DLWQIGJVBFVIJX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NPRDUFOUMDNSKG-UHFFFAOYSA-N 2-[[2-(2-methylpyrazol-3-yl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound CN1N=CC=C1C1=CC=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 NPRDUFOUMDNSKG-UHFFFAOYSA-N 0.000 claims 1
- AUAMYQVLPQXWEY-UHFFFAOYSA-N 2-[[2-(3,5-dimethylpyrazol-1-yl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound N1=C(C)C=C(C)N1C1=CC=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 AUAMYQVLPQXWEY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CXETUYDQSRGNBG-UHFFFAOYSA-N 2-[[2-(furan-2-yl)phenyl]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)N1CC1=CC=CC=C1C1=CC=CO1 CXETUYDQSRGNBG-UHFFFAOYSA-N 0.000 claims 1
- YIFFQRQHBGUUQF-UHFFFAOYSA-N 2-[[2-(furan-3-yl)-5-methyl-1,3-oxazol-4-yl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound N=1C(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C(C)OC=1C=1C=COC=1 YIFFQRQHBGUUQF-UHFFFAOYSA-N 0.000 claims 1
- ZRMPAGQAVPAOQU-UHFFFAOYSA-N 2-[[2-methyl-5-(3-methylphenyl)-1,3-thiazol-4-yl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound S1C(C)=NC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1C1=CC=CC(C)=C1 ZRMPAGQAVPAOQU-UHFFFAOYSA-N 0.000 claims 1
- BETCEEBWLSLULS-UHFFFAOYSA-N 2-[[2-methyl-5-(triazol-2-yl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=C(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)C(C)=CC=C1N1N=CC=N1 BETCEEBWLSLULS-UHFFFAOYSA-N 0.000 claims 1
- PDSZTVUWMRKGKW-UHFFFAOYSA-N 2-[[3-(3-methoxyphenyl)imidazol-4-yl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound COC1=CC=CC(N2C(=CN=C2)CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 PDSZTVUWMRKGKW-UHFFFAOYSA-N 0.000 claims 1
- YDZDZQBHJHYWCU-UHFFFAOYSA-N 2-[[3-(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=C(CN3C(C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCC3)=O)C=CC=2)=N1 YDZDZQBHJHYWCU-UHFFFAOYSA-N 0.000 claims 1
- WZSOKZAEGPUOGO-UHFFFAOYSA-N 2-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O1C(C)=NC(C=2C=C(CN3C(C4(CCN(CC4)C=4N=C5C=CC=CC5=NC=4)CCC3)=O)C=CC=2)=N1 WZSOKZAEGPUOGO-UHFFFAOYSA-N 0.000 claims 1
- MKKQACCARCNABB-UHFFFAOYSA-N 2-[[3-(5-methyl-1,3-oxazol-2-yl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O1C(C)=CN=C1C1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 MKKQACCARCNABB-UHFFFAOYSA-N 0.000 claims 1
- GDPWRMYMKQBVEF-UHFFFAOYSA-N 2-[[3-(methoxymethyl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound COCC1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 GDPWRMYMKQBVEF-UHFFFAOYSA-N 0.000 claims 1
- MMHJLDCGMNAMDJ-UHFFFAOYSA-N 2-[[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O1C(C)=NN=C1C(C=C1)=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 MMHJLDCGMNAMDJ-UHFFFAOYSA-N 0.000 claims 1
- DPSCLWDDYMNDKJ-UHFFFAOYSA-N 2-[[5-(3-fluorophenyl)-2-methyl-1,3-thiazol-4-yl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound S1C(C)=NC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1C1=CC=CC(F)=C1 DPSCLWDDYMNDKJ-UHFFFAOYSA-N 0.000 claims 1
- LPGIRLKYYQOUFT-UHFFFAOYSA-N 2-[[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC(OC)=CC=C1C(O1)=NN=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 LPGIRLKYYQOUFT-UHFFFAOYSA-N 0.000 claims 1
- GGLWIUOBEJAFRV-UHFFFAOYSA-N 2-[[5-methyl-2-(1,3-thiazol-4-yl)-1,3-oxazol-4-yl]methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound N=1C(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C(C)OC=1C1=CSC=N1 GGLWIUOBEJAFRV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GFXQGGGPTWXAKG-UHFFFAOYSA-N 2-benzyl-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)N1CC1=CC=CC=C1 GFXQGGGPTWXAKG-UHFFFAOYSA-N 0.000 claims 1
- FSOJBJBSRHWIQD-UHFFFAOYSA-N 2-fluoro-5-[(1-oxo-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-2-yl)methyl]benzonitrile;2-[(5-phenyl-1,3-oxazol-4-yl)methyl]-9-quinoxalin-2-yl-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=C(C#N)C(F)=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1.C1CCC2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)C(=O)N1CC=1N=COC=1C1=CC=CC=C1 FSOJBJBSRHWIQD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- NCTTZLPSBICNBE-UHFFFAOYSA-N 9-(1-methylbenzimidazol-2-yl)-2-(naphthalen-1-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(CN3CCCC4(CCN(CC4)C=4N(C5=CC=CC=C5N=4)C)C3=O)=CC=CC2=C1 NCTTZLPSBICNBE-UHFFFAOYSA-N 0.000 claims 1
- HOQZAIVCZMIJRG-UHFFFAOYSA-N 9-(1h-benzimidazol-2-yl)-1-(1h-indol-4-ylmethyl)-1,9-diazaspiro[5.5]undecan-2-one Chemical compound O=C1CCCC2(CCN(CC2)C=2NC3=CC=CC=C3N=2)N1CC1=CC=CC2=C1C=CN2 HOQZAIVCZMIJRG-UHFFFAOYSA-N 0.000 claims 1
- LQTAWFWESCZMLO-UHFFFAOYSA-N 9-(1h-benzimidazol-2-yl)-2-(1h-indol-3-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2NC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5NC=3)C4=O)=NC2=C1 LQTAWFWESCZMLO-UHFFFAOYSA-N 0.000 claims 1
- QVQBRELNCAXZCF-UHFFFAOYSA-N 9-(1h-benzimidazol-2-yl)-2-(naphthalen-1-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2NC(N3CCC4(CC3)CCCN(CC=3C5=CC=CC=C5C=CC=3)C4=O)=NC2=C1 QVQBRELNCAXZCF-UHFFFAOYSA-N 0.000 claims 1
- MYGHHCVTMJHSJV-UHFFFAOYSA-N 9-(1h-benzimidazol-2-yl)-2-[(3-chlorophenyl)methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound ClC1=CC=CC(CN2C(C3(CCN(CC3)C=3NC4=CC=CC=C4N=3)CCC2)=O)=C1 MYGHHCVTMJHSJV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FSQNPAXUADPDOQ-UHFFFAOYSA-N 9-(5-chloro-1,3-benzoxazol-2-yl)-1-(1h-indol-4-ylmethyl)-1,9-diazaspiro[5.5]undecan-2-one Chemical compound N=1C2=CC(Cl)=CC=C2OC=1N(CC1)CCC21CCCC(=O)N2CC1=CC=CC2=C1C=CN2 FSQNPAXUADPDOQ-UHFFFAOYSA-N 0.000 claims 1
- VDNLUZHGEVTZNA-UHFFFAOYSA-N 9-(5-chloro-1,3-benzoxazol-2-yl)-2-(1h-indol-3-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=C2C(CN3CCCC4(CCN(CC4)C=4OC5=CC=C(C=C5N=4)Cl)C3=O)=CNC2=C1 VDNLUZHGEVTZNA-UHFFFAOYSA-N 0.000 claims 1
- CFOAWEGRMUFFPB-UHFFFAOYSA-N 9-(6-chloro-1,3-benzoxazol-2-yl)-1-(1h-indol-4-ylmethyl)-1,9-diazaspiro[5.5]undecan-2-one Chemical compound O1C2=CC(Cl)=CC=C2N=C1N(CC1)CCC21CCCC(=O)N2CC1=CC=CC2=C1C=CN2 CFOAWEGRMUFFPB-UHFFFAOYSA-N 0.000 claims 1
- QMSUSGONCRBQAK-UHFFFAOYSA-N 9-(6-imidazol-1-ylpyrimidin-4-yl)-2-(1h-indol-3-ylmethyl)-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=1N1C=CN=C1 QMSUSGONCRBQAK-UHFFFAOYSA-N 0.000 claims 1
- VCHZOAWSHZTYIE-UHFFFAOYSA-N 9-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-2-(1h-indol-3-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC(F)=CC=C1C1=CSC(N2CCC3(C(N(CC=4C5=CC=CC=C5NC=4)CCC3)=O)CC2)=N1 VCHZOAWSHZTYIE-UHFFFAOYSA-N 0.000 claims 1
- XLIKROKXPPGMKW-UHFFFAOYSA-N 9-furo[3,2-c]pyridin-4-yl-2-(1h-indol-3-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1N(CC=2C3=CC=CC=C3NC=2)CCCC1(CC1)CCN1C1=NC=CC2=C1C=CO2 XLIKROKXPPGMKW-UHFFFAOYSA-N 0.000 claims 1
- MQHDHIUJZFOSLL-UHFFFAOYSA-N 9-imidazo[1,2-b]pyridazin-6-yl-2-(1h-indol-3-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC2=NC=CN2N=C1N(CC1)CCC21CCCN(CC=1C3=CC=CC=C3NC=1)C2=O MQHDHIUJZFOSLL-UHFFFAOYSA-N 0.000 claims 1
- NTHSRNIGVOPACS-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-([1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl)-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC=CC2=NC(N3CCC4(CC3)CCCN(CC=3N5C=CC=CC5=NN=3)C4=O)=CN=C21 NTHSRNIGVOPACS-UHFFFAOYSA-N 0.000 claims 1
- YXEGXIRCKPMOAH-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[(2,2,8-trimethyl-4h-[1,3]dioxino[4,5-c]pyridin-5-yl)methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1OC(C)(C)OC2=C1C(CN1C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC1)=O)=CN=C2C YXEGXIRCKPMOAH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LAZFQQSOMFUUKF-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[[2-(trifluoromethyl)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound FC(F)(F)C1=CC=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 LAZFQQSOMFUUKF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- PCRQKFMWHPQKKH-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[[3-(trifluoromethyl)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound FC(F)(F)C1=CC=CC(CN2C(C3(CCN(CC3)C=3N=C4C=CC=CC4=NC=3)CCC2)=O)=C1 PCRQKFMWHPQKKH-UHFFFAOYSA-N 0.000 claims 1
- UAHFHOYJLIYZAC-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[[4-(1,2,4-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=C1)=CC=C1N1C=NC=N1 UAHFHOYJLIYZAC-UHFFFAOYSA-N 0.000 claims 1
- FCXXOWPTWKBPCU-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[[4-(trifluoromethyl)phenyl]methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 FCXXOWPTWKBPCU-UHFFFAOYSA-N 0.000 claims 1
- ZSCZCJVMOOTQIH-UHFFFAOYSA-N 9-quinoxalin-2-yl-2-[[6-(trifluoromethyl)pyridin-3-yl]methyl]-2,9-diazaspiro[5.5]undecan-1-one Chemical compound C1=NC(C(F)(F)F)=CC=C1CN1C(=O)C2(CCN(CC2)C=2N=C3C=CC=CC3=NC=2)CCC1 ZSCZCJVMOOTQIH-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- GNECVGVZEFKCTH-UHFFFAOYSA-N O=C1N(Cc2cccc(c2)C#N)CCCC11CCN(CC1)c1cnc2ccccc2n1.O=C1N(Cc2nccc3ccccc23)CCCC11CCN(CC1)c1cnc2ccccc2n1 Chemical compound O=C1N(Cc2cccc(c2)C#N)CCCC11CCN(CC1)c1cnc2ccccc2n1.O=C1N(Cc2nccc3ccccc23)CCCC11CCN(CC1)c1cnc2ccccc2n1 GNECVGVZEFKCTH-UHFFFAOYSA-N 0.000 claims 1
- PQVPQPBBGMLCSB-UHFFFAOYSA-N O=C1N(Cc2ccccc2C#N)CCCC11CCN(CC1)c1cnc2ccccc2n1.Cc1ccc(c(CN2CCCC3(CCN(CC3)c3cnc4ccccc4n3)C2=O)c1)-n1nccn1 Chemical compound O=C1N(Cc2ccccc2C#N)CCCC11CCN(CC1)c1cnc2ccccc2n1.Cc1ccc(c(CN2CCCC3(CCN(CC3)c3cnc4ccccc4n3)C2=O)c1)-n1nccn1 PQVPQPBBGMLCSB-UHFFFAOYSA-N 0.000 claims 1
- 108050000742 Orexin Receptor Proteins 0.000 claims 1
- 102000008834 Orexin receptor Human genes 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000004630 mental health Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 102000002512 Orexin Human genes 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 239000012131 assay buffer Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 108060005714 orexin Proteins 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 2
- 229960003081 probenecid Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- ULFMXDSKSOVKQT-UHFFFAOYSA-N (3-pyrazin-2-ylphenyl)methanol Chemical compound OCC1=CC=CC(C=2N=CC=NC=2)=C1 ULFMXDSKSOVKQT-UHFFFAOYSA-N 0.000 description 1
- SPJUDCNSCRCKDN-UHFFFAOYSA-N 2-[3-(bromomethyl)phenyl]pyrazine Chemical compound BrCC1=CC=CC(C=2N=CC=NC=2)=C1 SPJUDCNSCRCKDN-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QOMNQGZXFYNBNG-UHFFFAOYSA-N acetyloxymethyl 2-[2-[2-[5-[3-(acetyloxymethoxy)-2,7-difluoro-6-oxoxanthen-9-yl]-2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]phenoxy]ethoxy]-n-[2-(acetyloxymethoxy)-2-oxoethyl]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(F)C(=O)C=C3OC3=CC(OCOC(C)=O)=C(F)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O QOMNQGZXFYNBNG-UHFFFAOYSA-N 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- OFNHNCAUVYOTPM-IIIOAANCSA-N orexin-a Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1NC(=O)[C@H](CO)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N2)[C@@H](C)O)=O)CSSC1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H]1NC(=O)CC1)C1=CNC=N1 OFNHNCAUVYOTPM-IIIOAANCSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000002731 protein assay Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2663/DEL/2009 | 2009-12-21 | ||
| IN2663DE2009 | 2009-12-21 | ||
| PCT/EP2010/070263 WO2011076747A1 (en) | 2009-12-21 | 2010-12-20 | Diaza-spiro[5.5]undecanes as orexin receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013515033A JP2013515033A (ja) | 2013-05-02 |
| JP2013515033A5 true JP2013515033A5 (enExample) | 2014-01-30 |
Family
ID=43640117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012545277A Pending JP2013515033A (ja) | 2009-12-21 | 2010-12-20 | 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 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8530648B2 (enExample) |
| EP (1) | EP2516439B1 (enExample) |
| JP (1) | JP2013515033A (enExample) |
| CN (1) | CN102762567A (enExample) |
| AR (1) | AR079553A1 (enExample) |
| ES (1) | ES2459496T3 (enExample) |
| TW (1) | TW201132642A (enExample) |
| UY (1) | UY33125A (enExample) |
| WO (1) | WO2011076747A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120101110A1 (en) * | 2010-10-26 | 2012-04-26 | Sangamesh Badiger | Diaza-spiro[5.5]undecanes |
| US20120165331A1 (en) * | 2010-12-22 | 2012-06-28 | Sangamesh Badiger | Di/tri-aza-spiro-C9-C11alkanes |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| RU2014136339A (ru) | 2012-02-07 | 2016-03-27 | Иолас Терапьютикс, Инк. | Замещенные пролины/пиперидины как антагонисты орексиновых рецепторов |
| ITMI20120424A1 (it) | 2012-03-19 | 2013-09-20 | Rottapharm Spa | Composti chimici |
| CA2945687A1 (en) * | 2014-01-27 | 2015-07-30 | Allergan, Inc. | Antagonists acting at multiple prostaglandin receptors for the treatment of inflammation |
| JP2017100951A (ja) * | 2014-04-04 | 2017-06-08 | 大正製薬株式会社 | オキサゾリジノン及びオキサジナノン誘導体 |
| EP3180332B1 (en) | 2014-08-13 | 2021-10-27 | Eolas Therapeutics Inc. | Difluoropyrrolidines as orexin receptor modulators |
| US10196383B2 (en) | 2015-07-17 | 2019-02-05 | Sunshine Lake Pharma Co., Ltd. | Substituted quinazoline compounds and preparation and uses thereof |
| KR102738491B1 (ko) | 2016-02-12 | 2024-12-03 | 아스트라제네카 아베 | 오렉신 수용체 조정제로서의 할로-치환된 피페리딘 |
| BR112019001921A2 (pt) | 2016-08-01 | 2019-05-14 | Aptinyx Inc. | moduladores do receptor nmda de espiro-lactama e seus usos |
| SG11201900554YA (en) | 2016-08-01 | 2019-02-27 | Aptinyx Inc | Spiro-lactam nmda modulators and methods of using same |
| AU2017306152A1 (en) | 2016-08-01 | 2019-01-31 | Aptinyx Inc. | Spiro-lactam NMDA receptor modulators and uses thereof |
| CN106831774B (zh) * | 2017-02-07 | 2019-02-01 | 上海合全药业股份有限公司 | 一种(6s，7s)-9-叔丁氧羰基-7-(三氟甲基)-2，9-二氮杂螺[5.5]十一烷的合成方法 |
| US11578072B2 (en) * | 2018-01-31 | 2023-02-14 | Aptinyx Inc. | Spiro-lactam NMDA receptor modulators and uses thereof |
| SG11202106108WA (en) * | 2019-01-28 | 2021-08-30 | Suntory Holdings Ltd | Composition for competitive inhibition of orexin receptors |
| EP4196478A1 (en) | 2020-08-14 | 2023-06-21 | Novartis AG | Heteroaryl substituted spiropiperidinyl derivatives and pharmaceutical uses thereof |
| US20240254143A1 (en) * | 2021-05-03 | 2024-08-01 | Jazz Pharmaceuticals Ireland Limited | Orexin receptor agonists and uses thereof |
| CA3236104A1 (en) * | 2021-10-27 | 2023-05-04 | Hugh Y. Zhu | Piperidinyl indole derivatives, preparation methods and medicinal uses thereof |
| WO2023081094A1 (en) * | 2021-11-04 | 2023-05-11 | University Of Washington | Novel spirocyclic compounds as klhdc2 ligands |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| JP4496722B2 (ja) * | 2002-06-28 | 2010-07-07 | 萬有製薬株式会社 | 新規ベンズイミダゾール誘導体 |
| CA2514733A1 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| JP2009506061A (ja) * | 2005-08-26 | 2009-02-12 | メルク エンド カムパニー インコーポレーテッド | ジアザスピロデカンオレキシン受容体拮抗薬 |
| WO2007058322A1 (ja) * | 2005-11-18 | 2007-05-24 | Ono Pharmaceutical Co., Ltd. | 塩基性基を含有する化合物およびその用途 |
-
2010
- 2010-12-20 ES ES10805703.5T patent/ES2459496T3/es active Active
- 2010-12-20 TW TW099144804A patent/TW201132642A/zh unknown
- 2010-12-20 JP JP2012545277A patent/JP2013515033A/ja active Pending
- 2010-12-20 US US13/517,111 patent/US8530648B2/en not_active Expired - Fee Related
- 2010-12-20 CN CN2010800643044A patent/CN102762567A/zh active Pending
- 2010-12-20 EP EP10805703.5A patent/EP2516439B1/en not_active Not-in-force
- 2010-12-20 AR ARP100104775A patent/AR079553A1/es unknown
- 2010-12-20 WO PCT/EP2010/070263 patent/WO2011076747A1/en not_active Ceased
- 2010-12-21 UY UY33125A patent/UY33125A/xx not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013515033A5 (enExample) | ||
| KR101811549B1 (ko) | 인돌린-2-온 또는 피롤로-피리딘/피리미딘-2-온 유도체 | |
| KR100854174B1 (ko) | Ｇａｂａ 수용체에 대한 리간드로서의 벤즈이미다졸 및피리딜이미다졸 유도체 | |
| JP5039268B2 (ja) | ベンゾイミダゾールおよび類縁体および蛋白キナーゼ阻害剤としてのその使用 | |
| JP7357932B2 (ja) | Ｃｒｈｒ２拮抗薬としての縮合環状尿素誘導体 | |
| JP2013515032A5 (enExample) | ||
| JP2013515033A (ja) | 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 | |
| JP2019504821A (ja) | ユビキチン特異的プロテアーゼ１阻害剤としてのプリノン | |
| WO2016033445A1 (en) | Probes for imaging huntingtin protein | |
| WO2015017610A1 (en) | Syk inhibitors | |
| US20170107204A1 (en) | Trka kinase inhibitors, compositions and methods thereof | |
| EP2601189A1 (en) | N-((6-amino-pyridin-3-yl)methyl)-heteroaryl-carboxamides as inhibitors of plasma kallikrein | |
| MX2010013920A (es) | Alcoholes alquinilicos como inhibidores de cinasas. | |
| KR20150143479A (ko) | Ｆａｓｎ 억제용 신규 화합물 및 조성물 | |
| US20120165331A1 (en) | Di/tri-aza-spiro-C9-C11alkanes | |
| US11814384B2 (en) | Inhibtors of Raf kinases | |
| EA037598B1 (ru) | Производные 3-((гетеро-)арил)-8-амино-2-оксо-1,3-диазаспиро[4,5]декана | |
| KR20150130311A (ko) | 야누스 키나제 억제제로서의 n-(2-시아노 헤테로시클릴)피라졸로 피리돈 | |
| JP2017226661A (ja) | 脆弱ｘ症候群、パーキンソン病又は逆流性疾患の治療に有用なジアゼピノン誘導体 | |
| TW202509019A (zh) | Sarm1調節子、其製劑及用途 | |
| RU2778641C2 (ru) | Производные конденсированной циклической мочевины в антагонист crhr2 | |
| HK40037565A (en) | Fused cyclic urea derivatives as crhr2 antagonist | |
| JPWO2022099144A5 (enExample) | ||
| HK40043109A (en) | Fused cyclic urea derivatives as crhr2 antagonist | |
| HK40043109B (en) | Fused cyclic urea derivatives as crhr2 antagonist |