CA2750106A1 - Poly (adp-ribose) polymerase (parp) inhibitors - Google Patents

Info

Publication number

CA2750106A1

CA2750106A1 CA2750106A CA2750106A CA2750106A1 CA 2750106 A1 CA2750106 A1 CA 2750106A1 CA 2750106 A CA2750106 A CA 2750106A CA 2750106 A CA2750106 A CA 2750106A CA 2750106 A1 CA2750106 A1 CA 2750106A1

Authority

CA

Canada

Prior art keywords

alkyl

hetero

methyl

pyrazin

cycloalkyl

Prior art date

2009-01-23

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 title claims abstract description 40
• 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 title description 39
• 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 title description 39
• 239000003112 inhibitor Substances 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 119
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
• 201000010099 disease Diseases 0.000 claims abstract description 33
• 238000000034 method Methods 0.000 claims abstract description 32
• 230000000694 effects Effects 0.000 claims abstract description 14
• 238000004519 manufacturing process Methods 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 claims abstract description 4
• 101710179684 Poly [ADP-ribose] polymerase Proteins 0.000 claims abstract 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 1289
• 125000005842 heteroatom Chemical group 0.000 claims description 1155
• 125000000217 alkyl group Chemical group 0.000 claims description 690
• 125000003118 aryl group Chemical group 0.000 claims description 526
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 519
• -1 cyano, thio, oxy, hydroxy, carbonyloxy Chemical group 0.000 claims description 303
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 267
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 245
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 241
• 125000005843 halogen group Chemical group 0.000 claims description 232
• 125000004104 aryloxy group Chemical group 0.000 claims description 219
• 229910052739 hydrogen Inorganic materials 0.000 claims description 179
• 239000001257 hydrogen Substances 0.000 claims description 179
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 127
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 126
• 125000003282 alkyl amino group Chemical group 0.000 claims description 121
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 121
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 121
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 121
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 120
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 110
• 125000003368 amide group Chemical group 0.000 claims description 88
• 125000005188 oxoalkyl group Chemical group 0.000 claims description 88
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 87
• 150000003839 salts Chemical class 0.000 claims description 48
• 125000004429 atom Chemical group 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000005647 linker group Chemical group 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 238000000926 separation method Methods 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 230000007170 pathology Effects 0.000 claims description 11
• 239000011593 sulfur Substances 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 238000011282 treatment Methods 0.000 claims description 5
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
• 206010028980 Neoplasm Diseases 0.000 claims description 3
• 206010063837 Reperfusion injury Diseases 0.000 claims description 3
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 230000000302 ischemic effect Effects 0.000 claims description 3
• 208000030159 metabolic disease Diseases 0.000 claims description 3
• 230000004770 neurodegeneration Effects 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 150000002431 hydrogen Chemical group 0.000 claims 40
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 29
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 11
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 11
• YPMPPDSCBNCBMX-FQEVSTJZSA-N (6S)-11-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound COC1=CC=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 YPMPPDSCBNCBMX-FQEVSTJZSA-N 0.000 claims 2
• KMPZMXZUCUWTIS-AWEZNQCLSA-N (3s)-3,4-dimethyl-7-[(3-oxo-4-phenylpiperazin-1-yl)methyl]-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound CN([C@H](C(NC1=C2)=O)C)C1=NC=C2CN(CC1=O)CCN1C1=CC=CC=C1 KMPZMXZUCUWTIS-AWEZNQCLSA-N 0.000 claims 1
• TXMTWVCKROOMCQ-HNNXBMFYSA-N (3s)-3,4-dimethyl-7-[(4-phenyl-3,6-dihydro-2h-pyridin-1-yl)methyl]-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound CN([C@H](C(NC1=C2)=O)C)C1=NC=C2CN(CC=1)CCC=1C1=CC=CC=C1 TXMTWVCKROOMCQ-HNNXBMFYSA-N 0.000 claims 1
• BGVDTDXNDKYCRK-HNNXBMFYSA-N (3s)-3,4-dimethyl-7-[(4-phenylpiperidin-1-yl)methyl]-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound CN([C@H](C(NC1=C2)=O)C)C1=NC=C2CN(CC1)CCC1C1=CC=CC=C1 BGVDTDXNDKYCRK-HNNXBMFYSA-N 0.000 claims 1
• UBBQGALHCSYCNY-ZETCQYMHSA-N (3s)-4-ethyl-7-(hydroxymethyl)-3-methyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound OCC1=CN=C2N(CC)[C@@H](C)C(=O)NC2=C1 UBBQGALHCSYCNY-ZETCQYMHSA-N 0.000 claims 1
• NCHRGLCDIMXRJI-QMMMGPOBSA-N (3s)-7-(hydroxymethyl)-3-methyl-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound OCC1=CN=C2N(C(C)C)[C@@H](C)C(=O)NC2=C1 NCHRGLCDIMXRJI-QMMMGPOBSA-N 0.000 claims 1
• WBPPIGHUYXKEGC-AWEZNQCLSA-N (3s)-7-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]-3,4-dimethyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound CN([C@H](C(NC1=C2)=O)C)C1=NC=C2CN(CC1)CCN1C1=CC=CC(Cl)=C1 WBPPIGHUYXKEGC-AWEZNQCLSA-N 0.000 claims 1
• BOPGTBFEFGUIGK-AWEZNQCLSA-N (3s)-7-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-3,4-dimethyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound CN([C@H](C(NC1=C2)=O)C)C1=NC=C2CN(CC=1)CCC=1C1=CC=C(Cl)C=C1 BOPGTBFEFGUIGK-AWEZNQCLSA-N 0.000 claims 1
• INOIQNQTCFAHRM-INIZCTEOSA-N (3s)-7-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-3-methyl-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound O=C([C@H](C)N(C1=NC=2)C(C)C)NC1=CC=2CN(CC=1)CCC=1C1=CC=C(Cl)C=C1 INOIQNQTCFAHRM-INIZCTEOSA-N 0.000 claims 1
• CDFLQJBYWUDOLH-HNNXBMFYSA-N (3s)-7-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-4-ethyl-3-methyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound O=C([C@H](C)N(C1=NC=2)CC)NC1=CC=2CN(CC=1)CCC=1C1=CC=C(Cl)C=C1 CDFLQJBYWUDOLH-HNNXBMFYSA-N 0.000 claims 1
• OGBCVWPITBPJQR-AWEZNQCLSA-N (3s)-7-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-3,4-dimethyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound CN([C@H](C(NC1=C2)=O)C)C1=NC=C2CN(CC1)CCN1C1=CC=C(Cl)C=C1 OGBCVWPITBPJQR-AWEZNQCLSA-N 0.000 claims 1
• CTDLYDGMMCFMQN-INIZCTEOSA-N (3s)-7-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-3-methyl-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound O=C([C@H](C)N(C1=NC=2)C(C)C)NC1=CC=2CN(CC1)CCN1C1=CC=C(Cl)C=C1 CTDLYDGMMCFMQN-INIZCTEOSA-N 0.000 claims 1
• NAVNWMMUWMBJTH-AWEZNQCLSA-N (3s)-7-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]-3,4-dimethyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound CN([C@H](C(NC1=C2)=O)C)C1=NC=C2CN(CC1)CCC1C1=CC=C(Cl)C=C1 NAVNWMMUWMBJTH-AWEZNQCLSA-N 0.000 claims 1
• AAPXHKLLFQGQLA-INIZCTEOSA-N (3s)-7-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]-3-methyl-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound O=C([C@H](C)N(C1=NC=2)C(C)C)NC1=CC=2CN(CC1)CCC1C1=CC=C(Cl)C=C1 AAPXHKLLFQGQLA-INIZCTEOSA-N 0.000 claims 1
• JAMFTDPPUXALOZ-AWEZNQCLSA-N (3s)-7-[[4-(4-fluorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-3,4-dimethyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound CN([C@H](C(NC1=C2)=O)C)C1=NC=C2CN(CC=1)CCC=1C1=CC=C(F)C=C1 JAMFTDPPUXALOZ-AWEZNQCLSA-N 0.000 claims 1
• 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
• MJJGVQPOMHATRF-IBGZPJMESA-N (6S)-11-[[4-(3-fluorophenyl)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=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 MJJGVQPOMHATRF-IBGZPJMESA-N 0.000 claims 1
• MXBLSEVTGZNSSS-IBGZPJMESA-N (6S)-11-[[4-(3-hydroxyphenyl)piperazin-1-yl]methyl]-2,8,13-triazatricyclo[7.4.0.02,6]trideca-1(9),10,12-trien-7-one Chemical compound OC1=CC=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 MXBLSEVTGZNSSS-IBGZPJMESA-N 0.000 claims 1
• ZTLZCQWFJJTRND-IBGZPJMESA-N (6S)-11-[[4-(4-bromophenyl)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(Br)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 ZTLZCQWFJJTRND-IBGZPJMESA-N 0.000 claims 1
• IUKPYGVCOTZNJC-IBGZPJMESA-N (6S)-11-[[4-(4-fluorophenyl)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(F)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 IUKPYGVCOTZNJC-IBGZPJMESA-N 0.000 claims 1
• OFJPCYCJJBQUAZ-IBGZPJMESA-N (6S)-11-[[4-(4-hydroxyphenyl)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(O)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 OFJPCYCJJBQUAZ-IBGZPJMESA-N 0.000 claims 1
• PAJSIHBWTQQZCZ-IBGZPJMESA-N (6S)-11-[[4-(4-iodophenyl)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(I)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 PAJSIHBWTQQZCZ-IBGZPJMESA-N 0.000 claims 1
• RYGHOHDSJUNRDM-FQEVSTJZSA-N (6S)-11-[[4-(4-methoxyphenyl)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(OC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 RYGHOHDSJUNRDM-FQEVSTJZSA-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
• OGEJCAQITDJFCB-VIFPVBQESA-N (6ar)-3-(hydroxymethyl)-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-6-one Chemical compound C1CSC[C@H]2C(=O)NC3=CC(CO)=CN=C3N21 OGEJCAQITDJFCB-VIFPVBQESA-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
• TUCORDXPZRSXKS-JTQLQIEISA-N (6as)-3-(hydroxymethyl)-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1CCC[C@H]2C(=O)NC3=CC(CO)=CN=C3N21 TUCORDXPZRSXKS-JTQLQIEISA-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
• UCNLBKQCXMQBTI-DEOSSOPVSA-N (6as)-3-[[4-[4-(5-oxocyclopenten-1-yl)phenyl]piperazin-1-yl]methyl]-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound O=C1CCC=C1C1=CC=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=C1 UCNLBKQCXMQBTI-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
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• AHAONXMHQCLKBJ-FQEVSTJZSA-N (s)-3-((1-(4-chlorophenyl)piperidin-4-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5h)-one Chemical compound C1=CC(Cl)=CC=C1N1CCC(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 AHAONXMHQCLKBJ-FQEVSTJZSA-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
• UBSMKZNLKPWBGT-IBGZPJMESA-N (s)-3-((4-phenylpiperazin-1-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5h)-one Chemical compound O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=CC=C1 UBSMKZNLKPWBGT-IBGZPJMESA-N 0.000 claims 1
• GUZFRSMBRGRKJT-QMMMGPOBSA-N (s)-3-(hydroxymethyl)-7,8-dihydro-5h-azeto[1,2-a]pyrido[3,2-e]pyrazin-6(6ah)-one Chemical compound O=C1NC2=CC(CO)=CN=C2N2CC[C@H]21 GUZFRSMBRGRKJT-QMMMGPOBSA-N 0.000 claims 1
• BBZNTXFDULPOGH-QMMMGPOBSA-N (s)-3-bromo-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5h)-one Chemical compound O=C1NC2=CC(Br)=CN=C2N2CCC[C@H]21 BBZNTXFDULPOGH-QMMMGPOBSA-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
• 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
• 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
• YAYJQNLWLSKJTB-QMMMGPOBSA-N (s)-methyl 6-oxo-6,6a,7,8-tetrahydro-5h-azeto[1,2-a]pyrido[3,2-e]pyrazine-3-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CN=C2N2CC[C@H]21 YAYJQNLWLSKJTB-QMMMGPOBSA-N 0.000 claims 1
• YHFQEXHSPMFQEW-NRFANRHFSA-N (s)-n,n-dimethyl-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)C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 YHFQEXHSPMFQEW-NRFANRHFSA-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
• 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
• 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
• JAFRSJFZGCKSQW-UHFFFAOYSA-N 10-oxo-1,3,4,9,10,10a-hexahydro-2,4-a,5,9-tetraaza-phenanthrene-2,7-dicarboxylic acid 2-tert-butyl ester 7-methyl ester Chemical compound C1CN(C(=O)OC(C)(C)C)CC2C(=O)NC3=CC(C(=O)OC)=CN=C3N21 JAFRSJFZGCKSQW-UHFFFAOYSA-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
• TUCORDXPZRSXKS-UHFFFAOYSA-N 3-(hydroxymethyl)-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-6-one Chemical compound C1CCCC2C(=O)NC3=CC(CO)=CN=C3N21 TUCORDXPZRSXKS-UHFFFAOYSA-N 0.000 claims 1
• AKUHVZVWKVWQGT-UHFFFAOYSA-N 3-(hydroxymethyl)-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]oxazin-6-one Chemical compound C1COCC2C(=O)NC3=CC(CO)=CN=C3N21 AKUHVZVWKVWQGT-UHFFFAOYSA-N 0.000 claims 1
• OGEJCAQITDJFCB-UHFFFAOYSA-N 3-(hydroxymethyl)-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-6-one Chemical compound C1CSCC2C(=O)NC3=CC(CO)=CN=C3N21 OGEJCAQITDJFCB-UHFFFAOYSA-N 0.000 claims 1
• RSFMTLLXTXTBPN-UHFFFAOYSA-N 3-(hydroxymethyl)-7a,8,9,10-tetrahydro-5h-pyrido[3,2-b]pyrrolo[1,2-d][1,4]diazepin-6(7h)-one Chemical compound C1C(=O)NC2=CC(CO)=CN=C2N2CCCC21 RSFMTLLXTXTBPN-UHFFFAOYSA-N 0.000 claims 1
• NVECEERIKZZHJS-UHFFFAOYSA-N 3-(hydroxymethyl)pyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5h)-one Chemical compound N1C(=O)C2=CC=CN2C2=NC=C(CO)C=C21 NVECEERIKZZHJS-UHFFFAOYSA-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
• VEHDJQRGPLBYQV-UHFFFAOYSA-N 3-[[4-(4-chlorophenyl)piperidin-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=C1C1CCN(CC=2C=C3NC(=O)C4CSCCN4C3=NC=2)CC1 VEHDJQRGPLBYQV-UHFFFAOYSA-N 0.000 claims 1
• OHSWJRXHQJWFSN-IBGZPJMESA-N 3-fluoro-5-[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]pyridine-2-carbonitrile Chemical compound N1=C(C#N)C(F)=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 OHSWJRXHQJWFSN-IBGZPJMESA-N 0.000 claims 1
• LPOIIMCWLISEDN-UHFFFAOYSA-N 4-(4-((6-oxo-6,7,7a,8,9,10-hexahydro-5h-pyrido[3,2-b]pyrrolo[1,2-d][1,4]diazepin-3-yl)methyl)piperazin-1-yl)benzonitrile Chemical compound C1=C2NC(=O)CC3CCCN3C2=NC=C1CN(CC1)CCN1C1=CC=C(C#N)C=C1 LPOIIMCWLISEDN-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
• MESJHBKIUFESFF-NRFANRHFSA-N 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]-3-chloro-n-ethylbenzamide Chemical compound ClC1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CSCCN4C3=NC=2)CC1 MESJHBKIUFESFF-NRFANRHFSA-N 0.000 claims 1
• WIXJAUIJSQETNB-FQEVSTJZSA-N 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]-3-chloro-n-methylbenzamide Chemical compound ClC1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CSCCN4C3=NC=2)CC1 WIXJAUIJSQETNB-FQEVSTJZSA-N 0.000 claims 1
• UHFLBVRQGQYQSY-QFIPXVFZSA-N 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]-n-cyclopropylbenzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CSCCN5C4=NC=3)CC2)C=CC=1C(=O)NC1CC1 UHFLBVRQGQYQSY-QFIPXVFZSA-N 0.000 claims 1
• JQYYPAOROSRKLY-NRFANRHFSA-N 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]-n-ethyl-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CSCCN4C3=NC=2)CC1 JQYYPAOROSRKLY-NRFANRHFSA-N 0.000 claims 1
• COYPKBHELNSTBR-NRFANRHFSA-N 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CSCCN4C3=NC=2)CC1 COYPKBHELNSTBR-NRFANRHFSA-N 0.000 claims 1
• CEQXKCUENVPGCC-FQEVSTJZSA-N 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CSCCN4C3=NC=2)CC1 CEQXKCUENVPGCC-FQEVSTJZSA-N 0.000 claims 1
• QMLGFBXRJBLSKM-IBGZPJMESA-N 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CSCCN4C3=NC=2)CC1 QMLGFBXRJBLSKM-IBGZPJMESA-N 0.000 claims 1
• MOKDCYQYOGLLTO-FQEVSTJZSA-N 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound O=C([C@@H]1CSCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=C1 MOKDCYQYOGLLTO-FQEVSTJZSA-N 0.000 claims 1
• HMIBWVZGECJHNF-QHCPKHFHSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-3-chloro-n-cyclopropylbenzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C(Cl)=CC=1C(=O)NC1CC1 HMIBWVZGECJHNF-QHCPKHFHSA-N 0.000 claims 1
• ZBIXBAYEOLPYRG-QFIPXVFZSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-3-chloro-n-ethylbenzamide Chemical compound ClC1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 ZBIXBAYEOLPYRG-QFIPXVFZSA-N 0.000 claims 1
• XPPZFNMKMXMGDQ-NRFANRHFSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-3-chloro-n-methylbenzamide Chemical compound ClC1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 XPPZFNMKMXMGDQ-NRFANRHFSA-N 0.000 claims 1
• NGGNIRQJTLCWRF-NRFANRHFSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-3-fluoro-n-methylbenzamide Chemical compound FC1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 NGGNIRQJTLCWRF-NRFANRHFSA-N 0.000 claims 1
• LABLKMYDBHRYDU-NRFANRHFSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-3-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 LABLKMYDBHRYDU-NRFANRHFSA-N 0.000 claims 1
• UFGWTMXWFVFDRS-QFIPXVFZSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n,3-dimethylbenzamide Chemical compound CC1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 UFGWTMXWFVFDRS-QFIPXVFZSA-N 0.000 claims 1
• UNWGULBHXJNLST-QHCPKHFHSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-cyclopropyl-3-fluorobenzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C(F)=CC=1C(=O)NC1CC1 UNWGULBHXJNLST-QHCPKHFHSA-N 0.000 claims 1
• WOUVFUKBYGEXOZ-DEOSSOPVSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-cyclopropyl-3-methylbenzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C(C)=CC=1C(=O)NC1CC1 WOUVFUKBYGEXOZ-DEOSSOPVSA-N 0.000 claims 1
• MACJUVPHLCKOSP-QHCPKHFHSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-cyclopropylbenzamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)C=CC=1C(=O)NC1CC1 MACJUVPHLCKOSP-QHCPKHFHSA-N 0.000 claims 1
• XQRVDZXDTHQKGA-QFIPXVFZSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-ethyl-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 XQRVDZXDTHQKGA-QFIPXVFZSA-N 0.000 claims 1
• LDMNYLXCFNARPT-QHCPKHFHSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-ethyl-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 LDMNYLXCFNARPT-QHCPKHFHSA-N 0.000 claims 1
• DDFRWELTTVRQAR-QFIPXVFZSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 DDFRWELTTVRQAR-QFIPXVFZSA-N 0.000 claims 1
• VCLLRFYIXDQALH-NRFANRHFSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 VCLLRFYIXDQALH-NRFANRHFSA-N 0.000 claims 1
• FGCMPNDBDHIPKZ-FQEVSTJZSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 FGCMPNDBDHIPKZ-FQEVSTJZSA-N 0.000 claims 1
• SOFYSVVCSBNXKC-NRFANRHFSA-N 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=C1 SOFYSVVCSBNXKC-NRFANRHFSA-N 0.000 claims 1
• ALRUAXSXYLAIBB-UHFFFAOYSA-N 4-benzyl-7-(hydroxymethyl)-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C1C(=O)NC2=CC(CO)=CN=C2N1CC1=CC=CC=C1 ALRUAXSXYLAIBB-UHFFFAOYSA-N 0.000 claims 1
• TYNOEVVRCHUMJZ-UHFFFAOYSA-N 4-benzyl-7-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N(CC=2C=CC=CC=2)CC(=O)N2)C2=C1 TYNOEVVRCHUMJZ-UHFFFAOYSA-N 0.000 claims 1
• QEZMDQJGHVJNKM-UHFFFAOYSA-N 4-benzyl-7-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)CN(CC=4C=CC=CC=4)C3=NC=2)CC1 QEZMDQJGHVJNKM-UHFFFAOYSA-N 0.000 claims 1
• BJDHHQRPDQTASK-UHFFFAOYSA-N 4-benzyl-7-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C1=CC(Cl)=CC=C1C1CCN(CC=2C=C3NC(=O)CN(CC=4C=CC=CC=4)C3=NC=2)CC1 BJDHHQRPDQTASK-UHFFFAOYSA-N 0.000 claims 1
• LZNRFJNVVOWKJW-UHFFFAOYSA-N 6-[4-[(6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]oxazin-3-yl)methyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C=1N=C2N3CCOCC3C(=O)NC2=CC=1CN(CC1)CCN1C1=CC=C(C#N)C=N1 LZNRFJNVVOWKJW-UHFFFAOYSA-N 0.000 claims 1
• GAWIEEZOQHXVNT-SFHVURJKSA-N 6-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound O=C([C@@H]1CSCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=N1 GAWIEEZOQHXVNT-SFHVURJKSA-N 0.000 claims 1
• FZWWANDEDKIQPP-NRFANRHFSA-N 6-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-cyclopropylpyridine-3-carboxamide Chemical compound C=1C=C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCCN5C4=NC=3)CC2)N=CC=1C(=O)NC1CC1 FZWWANDEDKIQPP-NRFANRHFSA-N 0.000 claims 1
• ZDGXRCQFKRVVIL-FQEVSTJZSA-N 6-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-ethylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 ZDGXRCQFKRVVIL-FQEVSTJZSA-N 0.000 claims 1
• SOMUEPFLWQLAHI-IBGZPJMESA-N 6-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 SOMUEPFLWQLAHI-IBGZPJMESA-N 0.000 claims 1
• CPIWDUPVMRMJGX-NRFANRHFSA-N 6-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]-n-propan-2-ylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC(C)C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 CPIWDUPVMRMJGX-NRFANRHFSA-N 0.000 claims 1
• RZRQRKRPOQCSTC-IBGZPJMESA-N 6-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound O=C([C@@H]1CCCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=N1 RZRQRKRPOQCSTC-IBGZPJMESA-N 0.000 claims 1
• KTAXABSTLWNGRL-SFHVURJKSA-N 6-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 KTAXABSTLWNGRL-SFHVURJKSA-N 0.000 claims 1
• MKJPWVHYSDHTML-UHFFFAOYSA-N 7-(hydroxymethyl)-4-methyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound OCC1=CN=C2N(C)CC(=O)NC2=C1 MKJPWVHYSDHTML-UHFFFAOYSA-N 0.000 claims 1
• QBUIYDFNOWVGSK-UHFFFAOYSA-N 7-(hydroxymethyl)-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound OCC1=CN=C2N(C(C)C)CC(=O)NC2=C1 QBUIYDFNOWVGSK-UHFFFAOYSA-N 0.000 claims 1
• DBNSANBLGQKATD-UHFFFAOYSA-N 7-[4-(4-chloro-phenyl)-piperazin-1-ylmethyl]-1,3,4,10a-tetrahydro-2h,9h-2,4-a,5,9-tetraaza-phenanthren-10-one Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)C4CNCCN4C3=NC=2)CC1 DBNSANBLGQKATD-UHFFFAOYSA-N 0.000 claims 1
• SVBGTYBZLYOQRB-UHFFFAOYSA-N 7-[4-(4-chloro-phenyl)-piperazin-1-ylmethyl]-10-oxo-1,3,4,9,10,10a-hexahydro-2,4-a,5,9-tetraaza-phenanthrene-2-carboxylic acid tert-butyl ester Chemical compound C1N(C(=O)OC(C)(C)C)CCN(C2=NC=3)C1C(=O)NC2=CC=3CN(CC1)CCN1C1=CC=C(Cl)C=C1 SVBGTYBZLYOQRB-UHFFFAOYSA-N 0.000 claims 1
• QNVJHMIXNGTKEZ-UHFFFAOYSA-N 7-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-4-methyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C=1N=C2N(C)CC(=O)NC2=CC=1CN(CC=1)CCC=1C1=CC=C(Cl)C=C1 QNVJHMIXNGTKEZ-UHFFFAOYSA-N 0.000 claims 1
• AHDYMCWKSWQNFX-UHFFFAOYSA-N 7-[[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]methyl]-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C=1N=C2N(C(C)C)CC(=O)NC2=CC=1CN(CC=1)CCC=1C1=CC=C(Cl)C=C1 AHDYMCWKSWQNFX-UHFFFAOYSA-N 0.000 claims 1
• KJHXSXCTGUDBEJ-UHFFFAOYSA-N 7-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-4-methyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C=1N=C2N(C)CC(=O)NC2=CC=1CN(CC1)CCN1C1=CC=C(Cl)C=C1 KJHXSXCTGUDBEJ-UHFFFAOYSA-N 0.000 claims 1
• ZDNXLEBMMQWSMP-UHFFFAOYSA-N 7-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C=1N=C2N(C(C)C)CC(=O)NC2=CC=1CN(CC1)CCN1C1=CC=C(Cl)C=C1 ZDNXLEBMMQWSMP-UHFFFAOYSA-N 0.000 claims 1
• KXVXYZWJASRLNJ-UHFFFAOYSA-N 7-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]-4-methyl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C=1N=C2N(C)CC(=O)NC2=CC=1CN(CC1)CCC1C1=CC=C(Cl)C=C1 KXVXYZWJASRLNJ-UHFFFAOYSA-N 0.000 claims 1
• JFXMCHAYNCLLKF-UHFFFAOYSA-N 7-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C=1N=C2N(C(C)C)CC(=O)NC2=CC=1CN(CC1)CCC1C1=CC=C(Cl)C=C1 JFXMCHAYNCLLKF-UHFFFAOYSA-N 0.000 claims 1
• JBTCCOBHGHULAO-SFHVURJKSA-N C1=C(C#N)C(F)=C(F)C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 Chemical compound C1=C(C#N)C(F)=C(F)C(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 JBTCCOBHGHULAO-SFHVURJKSA-N 0.000 claims 1
• RENADBZEQAMUML-IBGZPJMESA-N C1=C(Cl)C(F)=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 Chemical compound C1=C(Cl)C(F)=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 RENADBZEQAMUML-IBGZPJMESA-N 0.000 claims 1
• MNDBMHDIHFWZRD-NRFANRHFSA-N C1=CC(C(=O)C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 MNDBMHDIHFWZRD-NRFANRHFSA-N 0.000 claims 1
• WIAZQDYZWUNBEI-UHFFFAOYSA-N C1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3C(N4C=CC=C4C(=O)N3)=NC=2)CC1 Chemical compound C1=CC(C(=O)NCC)=CC=C1N1CCN(CC=2C=C3C(N4C=CC=C4C(=O)N3)=NC=2)CC1 WIAZQDYZWUNBEI-UHFFFAOYSA-N 0.000 claims 1
• FQFWHTMMXLGREM-FQEVSTJZSA-N C1=CC(C(=O)OC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 Chemical compound C1=CC(C(=O)OC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 FQFWHTMMXLGREM-FQEVSTJZSA-N 0.000 claims 1
• JZOZHLOLABSZBS-FQEVSTJZSA-N C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N2[C@@H](CCC2)C(=O)N2)C2=C1 Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N2[C@@H](CCC2)C(=O)N2)C2=C1 JZOZHLOLABSZBS-FQEVSTJZSA-N 0.000 claims 1
• JZOZHLOLABSZBS-HXUWFJFHSA-N C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N2[C@H](CCC2)C(=O)N2)C2=C1 Chemical compound C1=CC(Cl)=CC=C1C(CC1)=CCN1CC1=CN=C(N2[C@H](CCC2)C(=O)N2)C2=C1 JZOZHLOLABSZBS-HXUWFJFHSA-N 0.000 claims 1
• WBJHJWGWEXEORY-FQEVSTJZSA-N C1=CC(Cl)=CC=C1C1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 Chemical compound C1=CC(Cl)=CC=C1C1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 WBJHJWGWEXEORY-FQEVSTJZSA-N 0.000 claims 1
• WBJHJWGWEXEORY-HXUWFJFHSA-N C1=CC(Cl)=CC=C1C1CCN(CC=2C=C3NC(=O)[C@H]4CCCN4C3=NC=2)CC1 Chemical compound C1=CC(Cl)=CC=C1C1CCN(CC=2C=C3NC(=O)[C@H]4CCCN4C3=NC=2)CC1 WBJHJWGWEXEORY-HXUWFJFHSA-N 0.000 claims 1
• WHXMGWOZQZKVPH-UHFFFAOYSA-N C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)CC4CCCN4C3=NC=2)CC1 Chemical compound C1=CC(Cl)=CC=C1N1CCN(CC=2C=C3NC(=O)CC4CCCN4C3=NC=2)CC1 WHXMGWOZQZKVPH-UHFFFAOYSA-N 0.000 claims 1
• SDNBNPROTAHBEE-IBGZPJMESA-N C1=CC=C2NC(N3CCN(CC3)CC=3C=C4NC([C@@H]5CCCN5C4=NC=3)=O)=NC2=C1 Chemical compound C1=CC=C2NC(N3CCN(CC3)CC=3C=C4NC([C@@H]5CCCN5C4=NC=3)=O)=NC2=C1 SDNBNPROTAHBEE-IBGZPJMESA-N 0.000 claims 1
• WXBLLBRLSCXWGR-SFHVURJKSA-N C1=CC=C2OC(N3CCN(CC3)CC=3C=C4NC([C@@H]5CCCN5C4=NC=3)=O)=NC2=C1 Chemical compound C1=CC=C2OC(N3CCN(CC3)CC=3C=C4NC([C@@H]5CCCN5C4=NC=3)=O)=NC2=C1 WXBLLBRLSCXWGR-SFHVURJKSA-N 0.000 claims 1
• QBUCSPRGWDTWPG-PKHIMPSTSA-N C1CN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)C(C)CN1C1=CC=CC=N1 Chemical compound C1CN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)C(C)CN1C1=CC=CC=N1 QBUCSPRGWDTWPG-PKHIMPSTSA-N 0.000 claims 1
• RPZZZHOVIFMRSR-NRFANRHFSA-N CC1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 Chemical compound CC1=CC(C(=O)NC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 RPZZZHOVIFMRSR-NRFANRHFSA-N 0.000 claims 1
• DKWGEIRZJNQGTK-FQEVSTJZSA-N CC1=CC=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 Chemical compound CC1=CC=CC(N2CCN(CC=3C=C4NC(=O)[C@@H]5CCCN5C4=NC=3)CC2)=C1 DKWGEIRZJNQGTK-FQEVSTJZSA-N 0.000 claims 1
• KBKQCFJUIRKMAR-IBGZPJMESA-N FC1=CC(C#N)=CC(F)=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 Chemical compound FC1=CC(C#N)=CC(F)=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 KBKQCFJUIRKMAR-IBGZPJMESA-N 0.000 claims 1
• GMROVZNJSPVYKJ-KRWDZBQOSA-N N1=CC(C(F)(F)F)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCN4C3=NC=2)CC1 GMROVZNJSPVYKJ-KRWDZBQOSA-N 0.000 claims 1
• QQALHMPYPPZKKK-FQEVSTJZSA-N O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=C1 Chemical compound O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=C1 QQALHMPYPPZKKK-FQEVSTJZSA-N 0.000 claims 1
• UXMVKWNIUJKWFR-SFHVURJKSA-N O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=N1 Chemical compound O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)C=N1 UXMVKWNIUJKWFR-SFHVURJKSA-N 0.000 claims 1
• ILTFFEOFCFQLET-IBGZPJMESA-N O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)N=C1 Chemical compound O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=C(C#N)N=C1 ILTFFEOFCFQLET-IBGZPJMESA-N 0.000 claims 1
• UOMSIABEOJIXCJ-KRWDZBQOSA-N O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=CC=N1 Chemical compound O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=CC=CC=N1 UOMSIABEOJIXCJ-KRWDZBQOSA-N 0.000 claims 1
• YTICAWSKYOQZOS-INIZCTEOSA-N O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=NC=CC=N1 Chemical compound O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=NC=CC=N1 YTICAWSKYOQZOS-INIZCTEOSA-N 0.000 claims 1
• LREQSRNGKCAJLQ-HNNXBMFYSA-N O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=NC=NC=N1 Chemical compound O=C([C@@H]1CCCN1C1=NC=2)NC1=CC=2CN(CC1)CCN1C1=NC=NC=N1 LREQSRNGKCAJLQ-HNNXBMFYSA-N 0.000 claims 1
• 239000013543 active substance Substances 0.000 claims 1
• DWHFRZOTMVVCMV-NRFANRHFSA-N ethyl 4-[4-[[(6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazin-3-yl]methyl]piperazin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CSCCN4C3=NC=2)CC1 DWHFRZOTMVVCMV-NRFANRHFSA-N 0.000 claims 1
• GIQIANZAUKMHHW-QFIPXVFZSA-N ethyl 4-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 GIQIANZAUKMHHW-QFIPXVFZSA-N 0.000 claims 1
• YQAWXWFWFOLCAI-FQEVSTJZSA-N ethyl 6-[4-[[(6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazin-3-yl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OCC)=CC=C1N1CCN(CC=2C=C3NC(=O)[C@@H]4CCCCN4C3=NC=2)CC1 YQAWXWFWFOLCAI-FQEVSTJZSA-N 0.000 claims 1
• UGBKZHFRJUBXSI-QMMMGPOBSA-N methyl (3s)-3-methyl-2-oxo-4-propan-2-yl-1,3-dihydropyrido[2,3-b]pyrazine-7-carboxylate Chemical compound CC(C)N1[C@@H](C)C(=O)NC2=CC(C(=O)OC)=CN=C21 UGBKZHFRJUBXSI-QMMMGPOBSA-N 0.000 claims 1
• XZNIHPCZNAPWKN-ZETCQYMHSA-N methyl (3s)-4-ethyl-3-methyl-2-oxo-1,3-dihydropyrido[2,3-b]pyrazine-7-carboxylate Chemical compound COC(=O)C1=CN=C2N(CC)[C@@H](C)C(=O)NC2=C1 XZNIHPCZNAPWKN-ZETCQYMHSA-N 0.000 claims 1
• VGRACUOCWSYRJG-VIFPVBQESA-N methyl (6ar)-6-oxo-6a,7,9,10-tetrahydro-5h-pyrido[1,2]pyrazino[4,6-a][1,4]thiazine-3-carboxylate Chemical compound C1CSC[C@H]2C(=O)NC3=CC(C(=O)OC)=CN=C3N21 VGRACUOCWSYRJG-VIFPVBQESA-N 0.000 claims 1
• HKSUMJSJYVVOQZ-JTQLQIEISA-N methyl (6as)-6-oxo-5,6a,7,8,9,10-hexahydrodipyrido[1,2-c:2',3'-f]pyrazine-3-carboxylate Chemical compound C1CCC[C@H]2C(=O)NC3=CC(C(=O)OC)=CN=C3N21 HKSUMJSJYVVOQZ-JTQLQIEISA-N 0.000 claims 1
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