JP5567599B2 - ポリ(adp−リボース)ポリメラーゼ(parp)阻害剤 - Google Patents
ポリ(adp−リボース)ポリメラーゼ(parp)阻害剤 Download PDFInfo
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- JP5567599B2 JP5567599B2 JP2011548104A JP2011548104A JP5567599B2 JP 5567599 B2 JP5567599 B2 JP 5567599B2 JP 2011548104 A JP2011548104 A JP 2011548104A JP 2011548104 A JP2011548104 A JP 2011548104A JP 5567599 B2 JP5567599 B2 JP 5567599B2
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- JP
- Japan
- Prior art keywords
- alkyl
- hetero
- methyl
- piperazin
- pyrazin
- 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.)
- Expired - Fee Related
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- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 title description 55
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 title description 55
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 title description 53
- 239000003112 inhibitor Substances 0.000 title description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 940
- 125000000217 alkyl group Chemical group 0.000 claims description 528
- 125000003118 aryl group Chemical group 0.000 claims description 376
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 362
- -1 cyano, thio, oxy, hydroxy, carbonyloxy Chemical group 0.000 claims description 294
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 226
- 150000001875 compounds Chemical class 0.000 claims description 202
- 125000004104 aryloxy group Chemical group 0.000 claims description 191
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 170
- 239000001257 hydrogen Substances 0.000 claims description 163
- 229910052739 hydrogen Inorganic materials 0.000 claims description 163
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 112
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 112
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 111
- 125000003282 alkyl amino group Chemical group 0.000 claims description 108
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 108
- 125000005843 halogen group Chemical group 0.000 claims description 103
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 98
- 229940124530 sulfonamide Drugs 0.000 claims description 85
- 150000003456 sulfonamides Chemical class 0.000 claims description 85
- 150000001408 amides Chemical class 0.000 claims description 82
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 78
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 67
- 150000003839 salts Chemical class 0.000 claims description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000004429 atom Chemical group 0.000 claims description 37
- 201000010099 disease Diseases 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 210000004369 blood Anatomy 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 208000030159 metabolic disease Diseases 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 3
- 208000028867 ischemia Diseases 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 20
- LAQJGAKLLZAETL-UHFFFAOYSA-N 2h-pyrazin-3-one Chemical compound O=C1CN=CC=N1 LAQJGAKLLZAETL-UHFFFAOYSA-N 0.000 claims 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 5
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- PPAJOMSDKOMGSS-LJQANCHMSA-N (6R)-11-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@H]4CCCN4C3=NC=2)CC1 PPAJOMSDKOMGSS-LJQANCHMSA-N 0.000 claims 1
- KZYUYYPRNXXFLG-SFHVURJKSA-N (6S)-11-[[(4-methoxyphenyl)methyl-methylamino]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound C1=CC(OC)=CC=C1CN(C)CC1=CN=C(N2[C@@H](CCC2)C(=O)N2)C2=C1 KZYUYYPRNXXFLG-SFHVURJKSA-N 0.000 claims 1
- ADUITFBJMQEAIZ-IBGZPJMESA-N (6S)-11-[[4-(3,5-difluorophenyl)piperazin-1-yl]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound FC1=CC(F)=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 ADUITFBJMQEAIZ-IBGZPJMESA-N 0.000 claims 1
- DDLJIHMEYVIBFH-FQEVSTJZSA-N (6S)-11-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound C1=CC(C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 DDLJIHMEYVIBFH-FQEVSTJZSA-N 0.000 claims 1
- MSBZQSMESRJKGX-KRWDZBQOSA-N (6S)-11-[[4-(5-chloropyridin-2-yl)piperazin-1-yl]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound N1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 MSBZQSMESRJKGX-KRWDZBQOSA-N 0.000 claims 1
- BNSGRNILDNFORU-IBGZPJMESA-N (6S)-11-[[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 BNSGRNILDNFORU-IBGZPJMESA-N 0.000 claims 1
- IQYXVRUKMCDRJI-KRWDZBQOSA-N (6S)-11-[[benzyl(methyl)amino]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(C)CC1=CC=CC=C1 IQYXVRUKMCDRJI-KRWDZBQOSA-N 0.000 claims 1
- OGOPSDDRTUDWAI-FQEVSTJZSA-N (6ar)-3-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-6-one Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N2[C@@H](CSCC2)C(=O)N2)C2=C1 OGOPSDDRTUDWAI-FQEVSTJZSA-N 0.000 claims 1
- AADZTGMNVAPJIK-FQEVSTJZSA-N (6as)-3-[[4-(4-bromophenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=CC(Br)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 AADZTGMNVAPJIK-FQEVSTJZSA-N 0.000 claims 1
- UHGFSXBAGNWYEP-NRFANRHFSA-N (6as)-3-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N2[C@@H](CCCC2)C(=O)N2)C2=C1 UHGFSXBAGNWYEP-NRFANRHFSA-N 0.000 claims 1
- SELQHPXHMAWJJK-FQEVSTJZSA-N (6as)-3-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 SELQHPXHMAWJJK-FQEVSTJZSA-N 0.000 claims 1
- RQZUMTAXPGLPTA-NRFANRHFSA-N (6as)-3-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=CC(Cl)=CC=C1C1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 RQZUMTAXPGLPTA-NRFANRHFSA-N 0.000 claims 1
- CMTDKKJGEUVCFN-SANMLTNESA-N (6as)-3-[[4-(4-phenylphenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C(C=C1)=CC=C1C1=CC=CC=C1 CMTDKKJGEUVCFN-SANMLTNESA-N 0.000 claims 1
- PEKGQBRIPBJYKL-DEOSSOPVSA-N (6as)-3-[[4-(4-pyrazin-2-ylphenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C(C=C1)=CC=C1C1=CN=CC=N1 PEKGQBRIPBJYKL-DEOSSOPVSA-N 0.000 claims 1
- AWIPFGOVKZAYBK-VWLOTQADSA-N (6as)-3-[[4-(4-pyridin-2-ylphenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C(C=C1)=CC=C1C1=CC=CC=N1 AWIPFGOVKZAYBK-VWLOTQADSA-N 0.000 claims 1
- NKKGGAZFAYKORV-VWLOTQADSA-N (6as)-3-[[4-(4-pyridin-3-ylphenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C(C=C1)=CC=C1C1=CC=CN=C1 NKKGGAZFAYKORV-VWLOTQADSA-N 0.000 claims 1
- HLRXLGWCCYHBOU-VWLOTQADSA-N (6as)-3-[[4-(4-pyridin-4-ylphenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C(C=C1)=CC=C1C1=CC=NC=C1 HLRXLGWCCYHBOU-VWLOTQADSA-N 0.000 claims 1
- YMEXLMCPEWLIMU-DEOSSOPVSA-N (6as)-3-[[4-(4-pyrimidin-5-ylphenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C(C=C1)=CC=C1C1=CN=CN=C1 YMEXLMCPEWLIMU-DEOSSOPVSA-N 0.000 claims 1
- DZVSBPFGVAVASI-QHCPKHFHSA-N (6as)-3-[[4-(4-thiophen-2-ylphenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C(C=C1)=CC=C1C1=CC=CS1 DZVSBPFGVAVASI-QHCPKHFHSA-N 0.000 claims 1
- PWQSVGZXVDVVLV-DEOSSOPVSA-N (6as)-3-[[4-(4-thiophen-3-ylphenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C(C=C1)=CC=C1C=1C=CSC=1 PWQSVGZXVDVVLV-DEOSSOPVSA-N 0.000 claims 1
- NVNLVHOZQOKXAM-DEOSSOPVSA-N (6as)-3-[[4-[4-(1-methylpyrazol-4-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=NN(C)C=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 NVNLVHOZQOKXAM-DEOSSOPVSA-N 0.000 claims 1
- YRDUYSLMGYOWPO-VWLOTQADSA-N (6as)-3-[[4-[4-(2-methoxypyridin-3-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound COC1=NC=CC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 YRDUYSLMGYOWPO-VWLOTQADSA-N 0.000 claims 1
- YRHBKZXXVMOEDZ-VWLOTQADSA-N (6as)-3-[[4-[4-(2-methoxypyridin-4-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=NC(OC)=CC(C=2C=CC(=CC=2)N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)=C1 YRHBKZXXVMOEDZ-VWLOTQADSA-N 0.000 claims 1
- MLUZYGPMYROSSB-DEOSSOPVSA-N (6as)-3-[[4-[4-(2-methoxypyrimidin-5-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=NC(OC)=NC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 MLUZYGPMYROSSB-DEOSSOPVSA-N 0.000 claims 1
- KHIKTQUSCVHPBH-MHZLTWQESA-N (6as)-3-[[4-[4-(2-methylphenyl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound CC1=CC=CC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 KHIKTQUSCVHPBH-MHZLTWQESA-N 0.000 claims 1
- AYHGSEVPRQAODK-SANMLTNESA-N (6as)-3-[[4-[4-(2-methylpyridin-4-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=NC(C)=CC(C=2C=CC(=CC=2)N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)=C1 AYHGSEVPRQAODK-SANMLTNESA-N 0.000 claims 1
- HRFDVWYZZDDOFB-VWLOTQADSA-N (6as)-3-[[4-[4-(3-methoxypyridin-4-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound COC1=CN=CC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 HRFDVWYZZDDOFB-VWLOTQADSA-N 0.000 claims 1
- IKOAINFXYHFHOM-SANMLTNESA-N (6as)-3-[[4-[4-(3-methylpyridin-4-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound CC1=CN=CC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 IKOAINFXYHFHOM-SANMLTNESA-N 0.000 claims 1
- JKRXKFBHDKBQCR-DEOSSOPVSA-N (6as)-3-[[4-[4-(3-methylthiophen-2-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=CSC(C=2C=CC(=CC=2)N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)=C1C JKRXKFBHDKBQCR-DEOSSOPVSA-N 0.000 claims 1
- AWKIAHXVBHQHPS-SANMLTNESA-N (6as)-3-[[4-[4-(4-methylpyridin-2-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound CC1=CC=NC(C=2C=CC(=CC=2)N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)=C1 AWKIAHXVBHQHPS-SANMLTNESA-N 0.000 claims 1
- ZPTQUNQCVZLEHK-VWLOTQADSA-N (6as)-3-[[4-[4-(4-methylthiophen-3-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound CC1=CSC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 ZPTQUNQCVZLEHK-VWLOTQADSA-N 0.000 claims 1
- WVFICLXFZQNNFP-DEOSSOPVSA-N (6as)-3-[[4-[4-(5-methylthiophen-2-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound S1C(C)=CC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 WVFICLXFZQNNFP-DEOSSOPVSA-N 0.000 claims 1
- PIMNAEQRVXQMJG-DEOSSOPVSA-N (6as)-3-[[4-[4-(6-aminopyridin-2-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)=N1 PIMNAEQRVXQMJG-DEOSSOPVSA-N 0.000 claims 1
- BDECMCAGCFNLOK-VWLOTQADSA-N (6as)-3-[[4-[4-(6-methoxypyridin-2-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)=N1 BDECMCAGCFNLOK-VWLOTQADSA-N 0.000 claims 1
- PVMFFIHFSCUCRG-VWLOTQADSA-N (6as)-3-[[4-[4-(6-methoxypyridin-3-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 PVMFFIHFSCUCRG-VWLOTQADSA-N 0.000 claims 1
- PGVYCKGGYHRELG-SANMLTNESA-N (6as)-3-[[4-[4-(6-methylpyridin-3-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=NC(C)=CC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 PGVYCKGGYHRELG-SANMLTNESA-N 0.000 claims 1
- VVNJNQRCXJMDLR-MHZLTWQESA-N (6as)-3-[[4-[4-[2-(hydroxymethyl)phenyl]phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound OCC1=CC=CC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 VVNJNQRCXJMDLR-MHZLTWQESA-N 0.000 claims 1
- IJUYDXJYENPXCJ-IBGZPJMESA-N (s)-3-((4-(2,4-difluorophenyl)piperazin-1-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5h)-one Chemical compound FC1=CC(F)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 IJUYDXJYENPXCJ-IBGZPJMESA-N 0.000 claims 1
- WXCXFGAVUXTISL-QHCPKHFHSA-N (s)-3-((4-(4-(pyrrolidine-1-carbonyl)phenyl)piperazin-1-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5h)-one Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)C=CC=1C(=O)N1CCCC1 WXCXFGAVUXTISL-QHCPKHFHSA-N 0.000 claims 1
- PPAJOMSDKOMGSS-IBGZPJMESA-N (s)-3-((4-(4-chlorophenyl)piperazin-1-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5h)-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 PPAJOMSDKOMGSS-IBGZPJMESA-N 0.000 claims 1
- VAPIWZBXOBGUHC-FQEVSTJZSA-N (s)-3-((4-(4-fluoro-2-methylphenyl)piperazin-1-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5h)-one Chemical compound CC1=CC(F)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 VAPIWZBXOBGUHC-FQEVSTJZSA-N 0.000 claims 1
- JXLUEBGLWGRHIZ-FQEVSTJZSA-N (s)-3-chloro-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzonitrile Chemical compound ClC1=CC(C#N)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 JXLUEBGLWGRHIZ-FQEVSTJZSA-N 0.000 claims 1
- FOQUHTKZQKLQFS-QFIPXVFZSA-N (s)-3-chloro-n-cyclopropyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)C(Cl)=CC=1C(=O)NC1CC1 FOQUHTKZQKLQFS-QFIPXVFZSA-N 0.000 claims 1
- OZTSXFIBVZAPEL-NRFANRHFSA-N (s)-3-chloro-n-ethyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound ClC1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 OZTSXFIBVZAPEL-NRFANRHFSA-N 0.000 claims 1
- FNVLKAYQAGIFKZ-QFIPXVFZSA-N (s)-3-chloro-n-isopropyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound ClC1=CC(C(=O)NC(C)C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 FNVLKAYQAGIFKZ-QFIPXVFZSA-N 0.000 claims 1
- KHZVOGCESIZZDS-FQEVSTJZSA-N (s)-3-chloro-n-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound ClC1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 KHZVOGCESIZZDS-FQEVSTJZSA-N 0.000 claims 1
- NAIXRQYFGYHGBG-FQEVSTJZSA-N (s)-3-fluoro-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzonitrile Chemical compound FC1=CC(C#N)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 NAIXRQYFGYHGBG-FQEVSTJZSA-N 0.000 claims 1
- MQNHZGGPZLIVLI-QFIPXVFZSA-N (s)-3-fluoro-n-isopropyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound FC1=CC(C(=O)NC(C)C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 MQNHZGGPZLIVLI-QFIPXVFZSA-N 0.000 claims 1
- QAMJZTLFBOPTNQ-FQEVSTJZSA-N (s)-3-fluoro-n-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound FC1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 QAMJZTLFBOPTNQ-FQEVSTJZSA-N 0.000 claims 1
- WQKKUQDJDLOLIP-NRFANRHFSA-N (s)-3-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzonitrile Chemical compound CC1=CC(C#N)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 WQKKUQDJDLOLIP-NRFANRHFSA-N 0.000 claims 1
- ZLGLBIIZJMUCHB-IBGZPJMESA-N (s)-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 ZLGLBIIZJMUCHB-IBGZPJMESA-N 0.000 claims 1
- CKGPVOCSMDTBML-IBGZPJMESA-N (s)-4-(4-((6-oxo-6,6a,7,8-tetrahydro-5h-azeto[1,2-a]pyrido[3,2-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzonitrile Chemical compound O=C([C@@H]1CCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=C1 CKGPVOCSMDTBML-IBGZPJMESA-N 0.000 claims 1
- IXVHGZHCZQMZNK-KRWDZBQOSA-N (s)-6-(4((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 IXVHGZHCZQMZNK-KRWDZBQOSA-N 0.000 claims 1
- XIWPJLUXWWVNST-QFIPXVFZSA-N (s)-n-cyclopropyl-3-fluoro-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)C(F)=CC=1C(=O)NC1CC1 XIWPJLUXWWVNST-QFIPXVFZSA-N 0.000 claims 1
- SVIWPAOOEMGLFF-QHCPKHFHSA-N (s)-n-cyclopropyl-3-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)b enzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)C(C)=CC=1C(=O)NC1CC1 SVIWPAOOEMGLFF-QHCPKHFHSA-N 0.000 claims 1
- IAELLELRCVJROM-QFIPXVFZSA-N (s)-n-cyclopropyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)C=CC=1C(=O)NC1CC1 IAELLELRCVJROM-QFIPXVFZSA-N 0.000 claims 1
- PLGCNXGZHVZFTB-FQEVSTJZSA-N (s)-n-cyclopropyl-6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)N=CC=1C(=O)NC1CC1 PLGCNXGZHVZFTB-FQEVSTJZSA-N 0.000 claims 1
- CUDNLGMXSRNASQ-FQEVSTJZSA-N (s)-n-ethyl-2,5-difluoro-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C1=C(F)C(C(=O)NCC)=CC(F)=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 CUDNLGMXSRNASQ-FQEVSTJZSA-N 0.000 claims 1
- FDBOAPDDGJJAHV-NRFANRHFSA-N (s)-n-ethyl-2-fluoro-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C1=C(F)C(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 FDBOAPDDGJJAHV-NRFANRHFSA-N 0.000 claims 1
- IQMHHPRPWRFIAR-NRFANRHFSA-N (s)-n-ethyl-3-fluoro-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound FC1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 IQMHHPRPWRFIAR-NRFANRHFSA-N 0.000 claims 1
- JDXBBXHDCDMRAI-QFIPXVFZSA-N (s)-n-ethyl-3-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound CC1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 JDXBBXHDCDMRAI-QFIPXVFZSA-N 0.000 claims 1
- JCJXAMFPGJGHDE-NRFANRHFSA-N (s)-n-ethyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 JCJXAMFPGJGHDE-NRFANRHFSA-N 0.000 claims 1
- QWHQAPPPWWIOIF-IBGZPJMESA-N (s)-n-ethyl-6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinamide Chemical compound N1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 QWHQAPPPWWIOIF-IBGZPJMESA-N 0.000 claims 1
- WUOPXLCELLIDBY-QFIPXVFZSA-N (s)-n-ethyl-n-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C1=CC(C(=O)N(C)CC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 WUOPXLCELLIDBY-QFIPXVFZSA-N 0.000 claims 1
- DUYXSWHPKVYAGO-QFIPXVFZSA-N (s)-n-isopropyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 DUYXSWHPKVYAGO-QFIPXVFZSA-N 0.000 claims 1
- DXFWZZTUEGKQMI-FQEVSTJZSA-N (s)-n-isopropyl-6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinamide Chemical compound N1=CC(C(=O)NC(C)C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 DXFWZZTUEGKQMI-FQEVSTJZSA-N 0.000 claims 1
- JGTZRVFJIMUKHO-FQEVSTJZSA-N (s)-n-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 JGTZRVFJIMUKHO-FQEVSTJZSA-N 0.000 claims 1
- WBQJYGLXKWXXQU-FQEVSTJZSA-N (s)-n-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 WBQJYGLXKWXXQU-FQEVSTJZSA-N 0.000 claims 1
- PVBIEGJRECSVFB-SFHVURJKSA-N (s)-n-methyl-6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinamide Chemical compound N1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 PVBIEGJRECSVFB-SFHVURJKSA-N 0.000 claims 1
- LCKZFXFTIFZJAD-UHFFFAOYSA-N 11-[[4-(4-chlorophenyl)-3,6-dihydro-2H-pyridin-1-yl]methyl]-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,10,12-pentaen-7-one Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C2N3C=NC=C3C(=O)NC2=C1 LCKZFXFTIFZJAD-UHFFFAOYSA-N 0.000 claims 1
- YTRWGCUVTKXDTR-UHFFFAOYSA-N 11-[[4-(4-chlorophenyl)-3,6-dihydro-2H-pyridin-1-yl]methyl]-2,5,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,10,12-pentaen-7-one Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C2N3C=CN=C3C(=O)NC2=C1 YTRWGCUVTKXDTR-UHFFFAOYSA-N 0.000 claims 1
- WYIZZTHRNWSIGO-IBGZPJMESA-N 2,5-difluoro-4-[4-[[(6S)-7-oxo-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-11-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1F WYIZZTHRNWSIGO-IBGZPJMESA-N 0.000 claims 1
- SJVFOPBDZKJRJN-FQEVSTJZSA-N 2,6-difluoro-4-[4-[[(6S)-7-oxo-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-11-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound FC1=C(C#N)C(F)=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 SJVFOPBDZKJRJN-FQEVSTJZSA-N 0.000 claims 1
- BQLWSBVKPIIDPB-FQEVSTJZSA-N 2-fluoro-4-[4-[[(6S)-7-oxo-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-11-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 BQLWSBVKPIIDPB-FQEVSTJZSA-N 0.000 claims 1
- UHGFSXBAGNWYEP-UHFFFAOYSA-N 3-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N2C(CCCC2)C(=O)N2)C2=C1 UHGFSXBAGNWYEP-UHFFFAOYSA-N 0.000 claims 1
- OGOPSDDRTUDWAI-UHFFFAOYSA-N 3-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-6-one Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N2C(CSCC2)C(=O)N2)C2=C1 OGOPSDDRTUDWAI-UHFFFAOYSA-N 0.000 claims 1
- SELQHPXHMAWJJK-UHFFFAOYSA-N 3-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)C4CCCCN4C3=NC=2)CC1 SELQHPXHMAWJJK-UHFFFAOYSA-N 0.000 claims 1
- ZNCNVTDISAFGOE-UHFFFAOYSA-N 3-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]oxazin-6-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)C4COCCN4C3=NC=2)CC1 ZNCNVTDISAFGOE-UHFFFAOYSA-N 0.000 claims 1
- OCCSDPKIBXLCRJ-UHFFFAOYSA-N 3-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-6-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)C4CSCCN4C3=NC=2)CC1 OCCSDPKIBXLCRJ-UHFFFAOYSA-N 0.000 claims 1
- RQZUMTAXPGLPTA-UHFFFAOYSA-N 3-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1=CC(Cl)=CC=C1C1CCN(CC=2C=C3NC(=O)C4CCCCN4C3=NC=2)CC1 RQZUMTAXPGLPTA-UHFFFAOYSA-N 0.000 claims 1
- YDFHXXPSBXGPSG-KKSFZXQISA-N 4-[(3s)-4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]-3-methylpiperazin-1-yl]benzonitrile Chemical compound C([C@@H](N(CC1)CC=2C=C3NC(=O)[C@@H]4CSCCN4C3=NC=2)C)N1C1=CC=C(C#N)C=C1 YDFHXXPSBXGPSG-KKSFZXQISA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
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| US61/228,879 | 2009-07-27 | ||
| PCT/US2010/021669 WO2010085570A1 (en) | 2009-01-23 | 2010-01-21 | Poly (ADP-Ribose) Polymerase (PARP) Inhibitors |
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