KR20160150292A - 이미다조피롤리디논 화합물 - Google Patents
이미다조피롤리디논 화합물 Download PDFInfo
- Publication number
- KR20160150292A KR20160150292A KR1020167035785A KR20167035785A KR20160150292A KR 20160150292 A KR20160150292 A KR 20160150292A KR 1020167035785 A KR1020167035785 A KR 1020167035785A KR 20167035785 A KR20167035785 A KR 20167035785A KR 20160150292 A KR20160150292 A KR 20160150292A
- Authority
- KR
- South Korea
- Prior art keywords
- chloro
- phenyl
- pyrrolo
- imidazol
- methyl
- 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.)
- Withdrawn
Links
- LOROIKRUMJLRJU-UHFFFAOYSA-N 4,6-dihydro-1h-pyrrolo[2,3-d]imidazol-5-one Chemical class N1C=NC2=C1CC(=O)N2 LOROIKRUMJLRJU-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 518
- 102000012199 E3 ubiquitin-protein ligase Mdm2 Human genes 0.000 claims abstract description 75
- 108050002772 E3 ubiquitin-protein ligase Mdm2 Proteins 0.000 claims abstract description 75
- 230000000694 effects Effects 0.000 claims abstract description 72
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 70
- 108050005300 MDM4 Proteins 0.000 claims abstract description 54
- 102000017274 MDM4 Human genes 0.000 claims abstract description 54
- 238000011282 treatment Methods 0.000 claims abstract description 48
- 201000010099 disease Diseases 0.000 claims abstract description 42
- 208000035475 disorder Diseases 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 230000001404 mediated effect Effects 0.000 claims abstract description 19
- -1 -isopropyl (4-chloro-phenyl) Imidazole-4-carboxylic acid Chemical compound 0.000 claims description 661
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 245
- 238000000034 method Methods 0.000 claims description 218
- 239000000543 intermediate Substances 0.000 claims description 214
- 150000003839 salts Chemical class 0.000 claims description 126
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 110
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 108
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 103
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 101
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 95
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 90
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 206010028980 Neoplasm Diseases 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 29
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- KEVRHVMWBKFGLO-UHFFFAOYSA-N 2,4-dimethoxypyrimidine Chemical compound COC1=CC=NC(OC)=N1 KEVRHVMWBKFGLO-UHFFFAOYSA-N 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 16
- 201000011510 cancer Diseases 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 12
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- ODEPCKAMZKHXMX-UHFFFAOYSA-N N1CNC2=C1C=NC2=O.COC2=NC=CC(=N2)OC Chemical compound N1CNC2=C1C=NC2=O.COC2=NC=CC(=N2)OC ODEPCKAMZKHXMX-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 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
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- FKMDHVOHDANIDG-UHFFFAOYSA-N 4-methoxy-n,n-dimethylpyrimidin-2-amine Chemical compound COC1=CC=NC(N(C)C)=N1 FKMDHVOHDANIDG-UHFFFAOYSA-N 0.000 claims description 4
- YNXLSFXQTQKQEF-UHFFFAOYSA-N 4-methoxypyrimidin-2-amine Chemical compound COC1=CC=NC(N)=N1 YNXLSFXQTQKQEF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- OJFZGVJIUAUOCL-UHFFFAOYSA-N 5-chloro-2-methyl-1,6-dihydropyrrolo[3,4-d]imidazol-4-one Chemical compound ClN1CC=2NC(=NC=2C1=O)C OJFZGVJIUAUOCL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- SUFDONJEDNTGFZ-UHFFFAOYSA-N CC(C=CC(Cl)=C1)=C1N1C(C(C=C2)=CC=C2Cl)=C2NCNC2C1=O Chemical compound CC(C=CC(Cl)=C1)=C1N1C(C(C=C2)=CC=C2Cl)=C2NCNC2C1=O SUFDONJEDNTGFZ-UHFFFAOYSA-N 0.000 claims description 4
- CAQXCTNNDRNNKD-UHFFFAOYSA-N COC1NC2=C(N1)C(=NC2=O)OC Chemical compound COC1NC2=C(N1)C(=NC2=O)OC CAQXCTNNDRNNKD-UHFFFAOYSA-N 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- PWRBCZZQRRPXAB-UHFFFAOYSA-N 3-chloropyridine Chemical compound ClC1=CC=CN=C1 PWRBCZZQRRPXAB-UHFFFAOYSA-N 0.000 claims description 3
- YGBFHERIAVTGCX-UHFFFAOYSA-N 4-[5-(5-chloro-2-methylphenyl)-2-(2-hydroxyphenyl)-6-oxo-3-propan-2-yl-4H-pyrrolo[3,4-d]imidazol-4-yl]benzonitrile Chemical compound C1=2N(C(C)C)C(C=3C(=CC=CC=3)O)=NC=2C(=O)N(C=2C(=CC=C(Cl)C=2)C)C1C1=CC=C(C#N)C=C1 YGBFHERIAVTGCX-UHFFFAOYSA-N 0.000 claims description 3
- BUZKJIRRFMMOIV-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-1,2,3,6a-tetrahydropyrrolo[3,4-d]imidazol-6-one Chemical compound ClC=1C(=C(C=CC=1)N1C(=C2NCNC2C1=O)C1=CC=C(C=C1)Cl)F BUZKJIRRFMMOIV-UHFFFAOYSA-N 0.000 claims description 3
- PEEKDNPLMDVAEH-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-6-(4-chlorophenyl)-1,6-dihydropyrrolo[3,4-d]imidazol-4-one Chemical compound ClC=1C=C(C=CC=1F)N1C(C=2NC=NC=2C1=O)C1=CC=C(C=C1)Cl PEEKDNPLMDVAEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- GVHLALQAMJGUGA-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-5,6-dihydro-1H-pyrrolo[3,4-d]imidazol-4-one Chemical compound NC1=NC=C(C(=N1)OC)C1=NC2=C(N1)CNC2=O GVHLALQAMJGUGA-UHFFFAOYSA-N 0.000 claims description 2
- QAYAOQFXJDGJCW-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)acetonitrile Chemical compound COC1=CC=C(CC#N)N=C1 QAYAOQFXJDGJCW-UHFFFAOYSA-N 0.000 claims description 2
- ZKMWZPFDSPCJMI-UHFFFAOYSA-N 2-[4-[5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-2-yl]-5-methoxypyridin-2-yl]acetonitrile Chemical compound COC1=CN=C(CC#N)C=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=C(Cl)C=CC=1)F)C2=O ZKMWZPFDSPCJMI-UHFFFAOYSA-N 0.000 claims description 2
- SPGQNOMPKOGAHP-UHFFFAOYSA-N 2-[4-[5-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-2-yl]-5-methoxypyridin-2-yl]acetonitrile Chemical compound COC1=CN=C(CC#N)C=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C=C(Cl)C(F)=CC=1)C2=O SPGQNOMPKOGAHP-UHFFFAOYSA-N 0.000 claims description 2
- FJJGHVXBAGOLIZ-UHFFFAOYSA-N 2-[5-[5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-2-yl]-6-methoxypyridin-3-yl]acetonitrile Chemical compound COC1=NC=C(CC#N)C=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=C(Cl)C=CC=1)F)C2=O FJJGHVXBAGOLIZ-UHFFFAOYSA-N 0.000 claims description 2
- FPZAXIDNSDUVHJ-UHFFFAOYSA-N 3-[5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=C(Cl)C=CC=1)F)C2=O FPZAXIDNSDUVHJ-UHFFFAOYSA-N 0.000 claims description 2
- LNNHALALUFFTDH-UHFFFAOYSA-N 3-[5-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-1H-pyrrolo[3,4-d]imidazol-2-yl]-4-methoxybenzamide Chemical compound ClC=1C=C(C=CC=1F)N1C(=C2N=C(NC2=C1)C=1C=C(C(=O)N)C=CC=1OC)C1=CC=C(C=C1)Cl LNNHALALUFFTDH-UHFFFAOYSA-N 0.000 claims description 2
- VMBMBKAFWBLORZ-UHFFFAOYSA-N 3-[5-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-2-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C=C(Cl)C(F)=CC=1)C2=O VMBMBKAFWBLORZ-UHFFFAOYSA-N 0.000 claims description 2
- MUVZQQBRCKNBCM-UHFFFAOYSA-N 3-chloro-2-fluoro-1,2,3a,5-tetrahydropyrrolo[3,4-d]imidazol-4-one Chemical compound ClN1C(NC=2C1C(NC=2)=O)F MUVZQQBRCKNBCM-UHFFFAOYSA-N 0.000 claims description 2
- KGXIGECSLXWHMJ-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-5-yl]-3-methylbenzamide Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC(=CC=1)C(N)=O)C)C2=O KGXIGECSLXWHMJ-UHFFFAOYSA-N 0.000 claims description 2
- DDIQYBKLJFOZCN-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-5-yl]-n-methylcyclohexane-1-carboxamide Chemical compound C1CC(C(=O)NC)CCC1N1C(=O)C(N=C(C=2C(=NC(OC)=NC=2)OC)N2C(C)C)=C2C1C1=CC=C(Cl)C=C1 DDIQYBKLJFOZCN-UHFFFAOYSA-N 0.000 claims description 2
- KICKGPNYIUHOAY-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-5-yl]-n-methylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC)CCC1N1C(=O)C(N=C(C=2C(=NC(OC)=NC=2)OC)N2C(C)C)=C2C1C1=CC=C(Cl)C=C1 KICKGPNYIUHOAY-UHFFFAOYSA-N 0.000 claims description 2
- OGQNROWARMVZRY-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-5-yl]cyclohexane-1-carboxylic acid Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C1CCC(CC1)C(O)=O)C2=O OGQNROWARMVZRY-UHFFFAOYSA-N 0.000 claims description 2
- ACCLSHZNFVKRDJ-UHFFFAOYSA-N 4-[5-(3-chloro-2-fluorophenyl)-2-(2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-4-yl]-3-methylbenzonitrile Chemical compound COC1=CC=CC=C1C(N1C(C)C)=NC2=C1C(C=1C(=CC(=CC=1)C#N)C)N(C=1C(=C(Cl)C=CC=1)F)C2=O ACCLSHZNFVKRDJ-UHFFFAOYSA-N 0.000 claims description 2
- GWDRXXNKBIDONN-UHFFFAOYSA-N 4-[5-(3-chloro-4-fluorophenyl)-2-(2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-4-yl]benzonitrile Chemical compound COC1=CC=CC=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(=CC=1)C#N)N(C=1C=C(Cl)C(F)=CC=1)C2=O GWDRXXNKBIDONN-UHFFFAOYSA-N 0.000 claims description 2
- OPBJFWASRUHSHW-UHFFFAOYSA-N 4-methoxy-n-methylpyrimidin-2-amine Chemical compound CNC1=NC=CC(OC)=N1 OPBJFWASRUHSHW-UHFFFAOYSA-N 0.000 claims description 2
- DKYCLMGWDCHJJO-UHFFFAOYSA-N 5-[5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-d]imidazol-2-yl]-6-methoxy-n,n-dimethylpyridazine-3-carboxamide Chemical compound COC1=NN=C(C(=O)N(C)C)C=C1C(N1C(C)C)=NC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=C(Cl)C=CC=1)F)C2=O DKYCLMGWDCHJJO-UHFFFAOYSA-N 0.000 claims description 2
- HLMYSMGUNFMRBM-UHFFFAOYSA-N 5-chloro-2-methyl-1,2,3,6a-tetrahydropyrrolo[3,4-d]imidazol-6-one Chemical compound ClN1C=C2NC(NC2C1=O)C HLMYSMGUNFMRBM-UHFFFAOYSA-N 0.000 claims description 2
- WAVRTRDWSFBQER-UHFFFAOYSA-N CC1=C(C=C(C=C1)Cl)N2C(C3=C(C2=O)N=CN3)C(C)C Chemical compound CC1=C(C=C(C=C1)Cl)N2C(C3=C(C2=O)N=CN3)C(C)C WAVRTRDWSFBQER-UHFFFAOYSA-N 0.000 claims description 2
- JDOXTVBUPQJDIJ-UHFFFAOYSA-N CC1=C(C=C(C=C1)Cl)N2C=C3C(=C2C4=CC=C(C=C4)Cl)N=C(N3)C5=C(C=NC(=C5)CC#N)OC Chemical compound CC1=C(C=C(C=C1)Cl)N2C=C3C(=C2C4=CC=C(C=C4)Cl)N=C(N3)C5=C(C=NC(=C5)CC#N)OC JDOXTVBUPQJDIJ-UHFFFAOYSA-N 0.000 claims description 2
- PUUOVIMYRBXCPJ-UHFFFAOYSA-N CC1=C(C=C(C=C1)Cl)N2C=C3C(=C2CC4=CC=C(C=C4)Cl)N=C(N3)C5=C(C=CC(=C5)C#N)OC Chemical compound CC1=C(C=C(C=C1)Cl)N2C=C3C(=C2CC4=CC=C(C=C4)Cl)N=C(N3)C5=C(C=CC(=C5)C#N)OC PUUOVIMYRBXCPJ-UHFFFAOYSA-N 0.000 claims description 2
- WAVRTRDWSFBQER-CQSZACIVSA-N CC1=C(C=C(C=C1)Cl)N2[C@@H](C3=C(C2=O)N=CN3)C(C)C Chemical compound CC1=C(C=C(C=C1)Cl)N2[C@@H](C3=C(C2=O)N=CN3)C(C)C WAVRTRDWSFBQER-CQSZACIVSA-N 0.000 claims description 2
- WAVRTRDWSFBQER-AWEZNQCLSA-N CC1=C(C=C(C=C1)Cl)N2[C@H](C3=C(C2=O)N=CN3)C(C)C Chemical compound CC1=C(C=C(C=C1)Cl)N2[C@H](C3=C(C2=O)N=CN3)C(C)C WAVRTRDWSFBQER-AWEZNQCLSA-N 0.000 claims description 2
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- DHNSTQKLLCLUOF-UHFFFAOYSA-N CC1=NC2=C(N1C)CN(C2=O)Cl Chemical compound CC1=NC2=C(N1C)CN(C2=O)Cl DHNSTQKLLCLUOF-UHFFFAOYSA-N 0.000 claims description 2
- JGTVSAWBZHVOAH-UHFFFAOYSA-N COC1=NC(=NC=C1C2=NC3=C(N2)C(NC3=O)C4=CC=C(C=C4)Cl)OC Chemical compound COC1=NC(=NC=C1C2=NC3=C(N2)C(NC3=O)C4=CC=C(C=C4)Cl)OC JGTVSAWBZHVOAH-UHFFFAOYSA-N 0.000 claims description 2
- CQAWOBCFBIKFRI-UHFFFAOYSA-N COC1NC2=C(N1)C=NC2=O Chemical compound COC1NC2=C(N1)C=NC2=O CQAWOBCFBIKFRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261591001P | 2012-01-26 | 2012-01-26 | |
| US61/591,001 | 2012-01-26 | ||
| US201261669902P | 2012-07-10 | 2012-07-10 | |
| US61/669,902 | 2012-07-10 | ||
| CNPCT/CN2012/086703 | 2012-12-14 | ||
| CNPCT/CN2012/086703 | 2012-12-14 | ||
| PCT/IB2013/050655 WO2013111105A1 (en) | 2012-01-26 | 2013-01-25 | Imidazopyrrolidinone compounds |
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