JP2013515033A5 - - Google Patents
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- 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
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- 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
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| US20120165331A1 (en) * | 2010-12-22 | 2012-06-28 | Sangamesh Badiger | Di/tri-aza-spiro-C9-C11alkanes |
| NZ628491A (en) | 2012-02-07 | 2016-06-24 | Eolas Therapeutics Inc | Substituted prolines / piperidines as orexin receptor antagonists |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| ITMI20120424A1 (it) | 2012-03-19 | 2013-09-20 | Rottapharm Spa | Composti chimici |
| EP3099667B1 (en) * | 2014-01-27 | 2017-11-01 | 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 |
| JP6663909B2 (ja) | 2014-08-13 | 2020-03-13 | エオラス セラピューティクス， インコーポレイテッド | オレキシンレセプターモジュレーターとしてのジフルオロピロリジン |
| US10196383B2 (en) | 2015-07-17 | 2019-02-05 | Sunshine Lake Pharma Co., Ltd. | Substituted quinazoline compounds and preparation and uses thereof |
| SI3414241T1 (sl) | 2016-02-12 | 2022-10-28 | Astrazeneca Ab | Halo-substituitani piperidini kot modulatorji receptorja oreksina |
| WO2018026798A1 (en) | 2016-08-01 | 2018-02-08 | Aptinyx Inc. | Spiro-lactam nmda modulators and methods of using same |
| ES2972533T3 (es) | 2016-08-01 | 2024-06-13 | Tenacia Biotechnology Hong Kong Co Ltd | Moduladores del receptor de NMDA a base de espirolactama, y sus usos |
| EA201990424A1 (ru) | 2016-08-01 | 2019-08-30 | Аптиникс Инк. | Спиролактамовые модуляторы nmda-рецептора и их применение |
| 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 |
| KR102761196B1 (ko) | 2018-01-31 | 2025-02-03 | 테나시아 바이오테크놀로지 (홍콩) 코., 리미티드 | 스피로-락탐 nmda 수용체 조정제 및 그의 용도 |
| AU2020216214A1 (en) * | 2019-01-28 | 2021-07-08 | Suntory Holdings Limited | Composition for competitive inhibition of orexin receptors |
| KR20230051227A (ko) | 2020-08-14 | 2023-04-17 | 노파르티스 아게 | 헤테로아릴 치환된 스피로피페리디닐 유도체 및 이의 제약 용도 |
| MX2023012971A (es) * | 2021-05-03 | 2024-01-16 | Jazz Pharmaceuticals Ireland Ltd | Agonistas del receptor de orexina y sus usos. |
| WO2023081094A1 (en) * | 2021-11-04 | 2023-05-11 | University Of Washington | Novel spirocyclic compounds as klhdc2 ligands |
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| 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 |
| 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 |
| US7105526B2 (en) * | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| 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 |
| US20090176789A1 (en) * | 2005-08-26 | 2009-07-09 | Breslin Michael J | Diazaspirodecane orexin receptor antagonists |
| PL1961744T3 (pl) * | 2005-11-18 | 2013-09-30 | Ono Pharmaceutical Co | Związek zawierający grupę zasadową oraz jego zastosowanie |
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