JP2003531210A5 - - Google Patents
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- Publication number
- JP2003531210A5 JP2003531210A5 JP2001578437A JP2001578437A JP2003531210A5 JP 2003531210 A5 JP2003531210 A5 JP 2003531210A5 JP 2001578437 A JP2001578437 A JP 2001578437A JP 2001578437 A JP2001578437 A JP 2001578437A JP 2003531210 A5 JP2003531210 A5 JP 2003531210A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridinyl
- diazabicyclo
- covalent bond
- compound
- pyrrole
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 177
- -1 nitro, 5-tetrazolyl Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 25
- 241000124008 Mammalia Species 0.000 claims description 22
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- BWQKEWGYFNUHHX-VXNVDRBHSA-N (1r,5s)-6-(6-bromo-5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Br)C(OC)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 BWQKEWGYFNUHHX-VXNVDRBHSA-N 0.000 claims description 4
- GCTVZTULKNGORX-PSASIEDQSA-N (1r,5s)-6-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(C)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 GCTVZTULKNGORX-PSASIEDQSA-N 0.000 claims description 4
- XHYQJTGLPJMMEB-PSASIEDQSA-N (1r,5s)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1([C@@H]2CNC[C@@H]2C1)C1=CC=CN=C1 XHYQJTGLPJMMEB-PSASIEDQSA-N 0.000 claims description 4
- UXNFBEZSLURUHM-ONGXEEELSA-N (1s,6r)-7-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(C)=CC(N2[C@H]3CNCC[C@H]3C2)=C1 UXNFBEZSLURUHM-ONGXEEELSA-N 0.000 claims description 4
- NHOKDBHEVHBXTJ-ONGXEEELSA-N (1s,6r)-7-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound N1([C@H]2CNCC[C@H]2C1)C1=CC=CN=C1 NHOKDBHEVHBXTJ-ONGXEEELSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 230000003957 neurotransmitter release Effects 0.000 claims description 4
- IWMPNPIMHCIYMC-HZGVNTEJSA-N (1r,5s)-6-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 IWMPNPIMHCIYMC-HZGVNTEJSA-N 0.000 claims description 3
- IQCDZVRYLPBQRD-CABZTGNLSA-N (1s,6r)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound COC1=CN=CC(N2[C@H]3CNCC[C@H]3C2)=C1 IQCDZVRYLPBQRD-CABZTGNLSA-N 0.000 claims description 3
- FZHVWHFLHSHANF-SCZZXKLOSA-N (3ar,6ar)-1-(6-chloropyridin-3-yl)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2CC1 FZHVWHFLHSHANF-SCZZXKLOSA-N 0.000 claims description 3
- NBPGBNNVEWLKEW-KOLCDFICSA-N (3ar,6ar)-1-pyridin-3-yl-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@@H]1CNC[C@@H]11)CN1C1=CC=CN=C1 NBPGBNNVEWLKEW-KOLCDFICSA-N 0.000 claims description 3
- DQHQCRQWOJTKBG-SCZZXKLOSA-N (3ar,6ar)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 DQHQCRQWOJTKBG-SCZZXKLOSA-N 0.000 claims description 3
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
- BSDFRUMXKRLPJN-NXEZZACHSA-N (1r,5r)-4-pyridin-3-yl-4,7-diazabicyclo[3.2.0]heptane Chemical compound C([C@H]1NC[C@@H]21)CN2C1=CC=CN=C1 BSDFRUMXKRLPJN-NXEZZACHSA-N 0.000 claims description 2
- CIYRARKCUJBDET-ZYHUDNBSSA-N (1r,5s)-6-(5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C#CC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 CIYRARKCUJBDET-ZYHUDNBSSA-N 0.000 claims description 2
- IBEGQZNIXSCPIN-LDYMZIIASA-N (1r,5s)-6-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound COC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 IBEGQZNIXSCPIN-LDYMZIIASA-N 0.000 claims description 2
- VXCWOKWPZDBULP-GMSGAONNSA-N (1r,6s)-7-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@@H]3CNCC[C@@H]3C2)=C1 VXCWOKWPZDBULP-GMSGAONNSA-N 0.000 claims description 2
- IQCDZVRYLPBQRD-BXKDBHETSA-N (1r,6s)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound COC1=CN=CC(N2[C@@H]3CNCC[C@@H]3C2)=C1 IQCDZVRYLPBQRD-BXKDBHETSA-N 0.000 claims description 2
- UXNFBEZSLURUHM-MWLCHTKSSA-N (1r,6s)-7-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(C)=CC(N2[C@@H]3CNCC[C@@H]3C2)=C1 UXNFBEZSLURUHM-MWLCHTKSSA-N 0.000 claims description 2
- NHOKDBHEVHBXTJ-MWLCHTKSSA-N (1r,6s)-7-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound N1([C@@H]2CNCC[C@@H]2C1)C1=CC=CN=C1 NHOKDBHEVHBXTJ-MWLCHTKSSA-N 0.000 claims description 2
- IWMPNPIMHCIYMC-RCOVLWMOSA-N (1s,5r)-6-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@H]3CNC[C@H]3C2)=C1 IWMPNPIMHCIYMC-RCOVLWMOSA-N 0.000 claims description 2
- CIYRARKCUJBDET-JQWIXIFHSA-N (1s,5r)-6-(5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C#CC1=CN=CC(N2[C@H]3CNC[C@H]3C2)=C1 CIYRARKCUJBDET-JQWIXIFHSA-N 0.000 claims description 2
- IBEGQZNIXSCPIN-KWQFWETISA-N (1s,5r)-6-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound COC1=CN=CC(N2[C@H]3CNC[C@H]3C2)=C1 IBEGQZNIXSCPIN-KWQFWETISA-N 0.000 claims description 2
- WBDWMCKZWXJEHV-ONGXEEELSA-N (1s,5r)-6-(6-bromo-5-ethenylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=C(C=C)C(Br)=NC=C1N1[C@H]2CNC[C@H]2C1 WBDWMCKZWXJEHV-ONGXEEELSA-N 0.000 claims description 2
- BWQKEWGYFNUHHX-CBAPKCEASA-N (1s,5r)-6-(6-bromo-5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Br)C(OC)=CC(N2[C@H]3CNC[C@H]3C2)=C1 BWQKEWGYFNUHHX-CBAPKCEASA-N 0.000 claims description 2
- GCTVZTULKNGORX-WPRPVWTQSA-N (1s,5r)-6-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(C)=CC(N2[C@H]3CNC[C@H]3C2)=C1 GCTVZTULKNGORX-WPRPVWTQSA-N 0.000 claims description 2
- XHYQJTGLPJMMEB-WPRPVWTQSA-N (1s,5r)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1([C@H]2CNC[C@H]2C1)C1=CC=CN=C1 XHYQJTGLPJMMEB-WPRPVWTQSA-N 0.000 claims description 2
- UYZGGVMCTYTMRJ-WCBMZHEXSA-N (1s,5s)-3-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound C([C@H]1NC[C@H]1C1)N1C1=CC=CN=C1 UYZGGVMCTYTMRJ-WCBMZHEXSA-N 0.000 claims description 2
- FDOUKQXLQIXJFX-ONGXEEELSA-N (1s,6r)-4-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound C([C@@H]1NC[C@@H]1CC1)N1C1=CC=CN=C1 FDOUKQXLQIXJFX-ONGXEEELSA-N 0.000 claims description 2
- QULYNSGTKPCWSF-XCBNKYQSSA-N (3ar,6ar)-5-(5,6-dichloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 QULYNSGTKPCWSF-XCBNKYQSSA-N 0.000 claims description 2
- FDUANQGPNHRGGA-YPMHNXCESA-N (3ar,6ar)-5-(5-ethynylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C#CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 FDUANQGPNHRGGA-YPMHNXCESA-N 0.000 claims description 2
- YSAVCILVSULFGD-SKDRFNHKSA-N (3ar,6ar)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound COC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 YSAVCILVSULFGD-SKDRFNHKSA-N 0.000 claims description 2
- ZCIPXINQRZWYCD-XCBNKYQSSA-N (3ar,6ar)-5-(6-bromo-5-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(Cl)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 ZCIPXINQRZWYCD-XCBNKYQSSA-N 0.000 claims description 2
- JCSPUVOHNHERBJ-PWSUYJOCSA-N (3ar,6ar)-5-(6-bromo-5-ethenylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C1=C(C=C)C(Br)=NC=C1N1C[C@@H]2NCC[C@@H]2C1 JCSPUVOHNHERBJ-PWSUYJOCSA-N 0.000 claims description 2
- SLNSBOHQJODUJZ-SCZZXKLOSA-N (3ar,6ar)-5-(6-bromo-5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(OC)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 SLNSBOHQJODUJZ-SCZZXKLOSA-N 0.000 claims description 2
- KEKVMZXOMNEOQP-KOLCDFICSA-N (3ar,6ar)-5-(6-bromo-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 KEKVMZXOMNEOQP-KOLCDFICSA-N 0.000 claims description 2
- RUEPBFNTOSWZAB-KOLCDFICSA-N (3ar,6ar)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 RUEPBFNTOSWZAB-KOLCDFICSA-N 0.000 claims description 2
- HMWDILXJWAOEJT-KOLCDFICSA-N (3ar,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@H]1CCN[C@H]1C1)N1C1=CC=CN=C1 HMWDILXJWAOEJT-KOLCDFICSA-N 0.000 claims description 2
- UBQWFBOLOFJCDH-PHIMTYICSA-N (3ar,6as)-2-methyl-5-pyridin-3-yl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole Chemical compound C([C@@H]1CN(C[C@@H]1C1)C)N1C1=CC=CN=C1 UBQWFBOLOFJCDH-PHIMTYICSA-N 0.000 claims description 2
- GUZUKHDQICFNFX-PHIMTYICSA-N (3ar,6as)-5-(5-ethoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound CCOC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 GUZUKHDQICFNFX-PHIMTYICSA-N 0.000 claims description 2
- OHWQUEIYHPZQPN-TXEJJXNPSA-N (3ar,6as)-5-(5-propoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound CCCOC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 OHWQUEIYHPZQPN-TXEJJXNPSA-N 0.000 claims description 2
- GGWINWDBVWLKNK-AOOOYVTPSA-N (3ar,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3CNC[C@H]3C2)=C1 GGWINWDBVWLKNK-AOOOYVTPSA-N 0.000 claims description 2
- QCAHYIYDXVYFOH-AOOOYVTPSA-N (3as,6ar)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound COC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 QCAHYIYDXVYFOH-AOOOYVTPSA-N 0.000 claims description 2
- VPFXUOCTXHVJCT-DTORHVGOSA-N (3as,6ar)-5-(6-chloro-5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound N1=C(Cl)C(OC)=CC(N2C[C@H]3CNC[C@H]3C2)=C1 VPFXUOCTXHVJCT-DTORHVGOSA-N 0.000 claims description 2
- WNQHCICGYPNPJA-DTORHVGOSA-N (3as,6ar)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1C[C@H]2CNC[C@H]2C1 WNQHCICGYPNPJA-DTORHVGOSA-N 0.000 claims description 2
- QZPCTRNKBFDOCH-AOOOYVTPSA-N (3as,6ar)-5-(6-chloropyridin-3-yl)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole Chemical compound C([C@@H]1CN(C[C@@H]1C1)C)N1C1=CC=C(Cl)N=C1 QZPCTRNKBFDOCH-AOOOYVTPSA-N 0.000 claims description 2
- KOMXDDRATCALPT-AOOOYVTPSA-N (3as,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound C([C@H]1CNC[C@H]1C1)N1C1=CC=CN=C1 KOMXDDRATCALPT-AOOOYVTPSA-N 0.000 claims description 2
- NBPGBNNVEWLKEW-GXSJLCMTSA-N (3as,6as)-1-pyridin-3-yl-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@H]1CNC[C@H]11)CN1C1=CC=CN=C1 NBPGBNNVEWLKEW-GXSJLCMTSA-N 0.000 claims description 2
- QULYNSGTKPCWSF-OIBJUYFYSA-N (3as,6as)-5-(5,6-dichloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(Cl)=CC(N2C[C@H]3NCC[C@H]3C2)=C1 QULYNSGTKPCWSF-OIBJUYFYSA-N 0.000 claims description 2
- YSAVCILVSULFGD-JOYOIKCWSA-N (3as,6as)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound COC1=CN=CC(N2C[C@H]3NCC[C@H]3C2)=C1 YSAVCILVSULFGD-JOYOIKCWSA-N 0.000 claims description 2
- RUEPBFNTOSWZAB-GXSJLCMTSA-N (3as,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3C2)=C1 RUEPBFNTOSWZAB-GXSJLCMTSA-N 0.000 claims description 2
- HMWDILXJWAOEJT-GXSJLCMTSA-N (3as,6as)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@@H]1CCN[C@@H]1C1)N1C1=CC=CN=C1 HMWDILXJWAOEJT-GXSJLCMTSA-N 0.000 claims description 2
- YETODIXQMRZKEG-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[2,3-c]pyrrole Chemical compound C1NCC2NCCC21 YETODIXQMRZKEG-UHFFFAOYSA-N 0.000 claims description 2
- WBIYGACFBGCOKV-PWSUYJOCSA-N 2-[5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-2-bromopyridin-3-yl]acetonitrile Chemical compound C1=C(CC#N)C(Br)=NC=C1N1C[C@@H]2NCC[C@@H]2C1 WBIYGACFBGCOKV-PWSUYJOCSA-N 0.000 claims description 2
- KQMSAFWRVJCRPS-PSASIEDQSA-N 2-bromo-5-[(1r,5s)-3,6-diazabicyclo[3.2.0]heptan-6-yl]pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Br)=NC=C1N1[C@@H]2CNC[C@@H]2C1 KQMSAFWRVJCRPS-PSASIEDQSA-N 0.000 claims description 2
- KLNHDAVAIWEDTG-BETUJISGSA-N 3-[(3ar,6as)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]quinoline Chemical compound C1=CC=CC2=CC(N3C[C@H]4CNC[C@H]4C3)=CN=C21 KLNHDAVAIWEDTG-BETUJISGSA-N 0.000 claims description 2
- KGHKOOLJKCBUSS-KOLCDFICSA-N 5-[(1r,5r)-3,6-diazabicyclo[3.2.0]heptan-3-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C[C@@H]3NC[C@@H]3C2)=C1 KGHKOOLJKCBUSS-KOLCDFICSA-N 0.000 claims description 2
- GPXAWLDGWSBLKM-MWLCHTKSSA-N 5-[(1r,5s)-3,6-diazabicyclo[3.2.0]heptan-6-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 GPXAWLDGWSBLKM-MWLCHTKSSA-N 0.000 claims description 2
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| CA2691782A1 (en) | 2007-09-11 | 2009-03-19 | Abbott Laboratories | Octahydro-pyrrolo[3,4-b]pyrrole n-oxides |
| UY31443A1 (es) | 2007-10-31 | 2009-04-30 | Diaminas en puente o fusionadas sustituidas con arilo como moduladores de leucotrieno a4 hidrolasa | |
| JP5628043B2 (ja) * | 2007-11-21 | 2014-11-19 | アッヴィ・インコーポレイテッド | ビアリール置換ジアザビシクロアルカン誘導体 |
| EP2623504A1 (de) | 2007-12-07 | 2013-08-07 | Abbott GmbH & Co. KG | 5,6-Disubstituierte Oxindol-Derivate und ihre Verwendung zur Herstellung eines Medikaments zur Behandlung von Vasopressin-abhängigen Erkrankungen |
| WO2009071687A1 (de) | 2007-12-07 | 2009-06-11 | Abbott Gmbh & Co. Kg | Amidomethyl-substituierte oxindol-derivate und ihre verwendung zur behandlung von vasopressin-abhängigen erkrankungen |
| CA2707669C (en) | 2007-12-07 | 2016-07-05 | Wilfried Braje | 5-halogen-substituted oxindole derivatives and use thereof for treating vasopressine-dependent diseases |
| US8703774B2 (en) | 2007-12-07 | 2014-04-22 | AbbVie Deutschland GmbH & Co. KG | Carbamate-substituted oxindole derivatives and use thereof for the treatment of vasopressin-dependent diseases |
| MX2010006111A (es) | 2007-12-18 | 2010-06-25 | Actelion Pharmaceuticals Ltd | Derivados de 5-aminociclilmetil-oxazolidin-2-ona y su uso como antibacteriales. |
| PT2336125E (pt) | 2008-04-11 | 2013-03-18 | Janssen Pharmaceutica Nv | Tiazolopiridina-2-iloxi-fenil e tiazolopirazin-2-iloxifenil aminas como moduladores de leucotrieno a4 hidrolase |
| US8148408B2 (en) * | 2008-05-09 | 2012-04-03 | Abbott Laboratories | Selective substituted pyridine ligands for neuronal nicotinic receptors |
| US8263632B2 (en) * | 2009-03-24 | 2012-09-11 | Vertex Pharmaceuticals Incoporated | Aminopyridine derivatives having Aurora A selective inhibitory action |
| WO2010132599A1 (en) | 2009-05-14 | 2010-11-18 | Janssen Pharmaceutica Nv | Compounds with two fused bicyclic heteroaryl moieties as modulators of leukotriene a4 hydrolase |
| WO2010138600A2 (en) | 2009-05-29 | 2010-12-02 | Abbott Laboratories | Pharmaceutical compositions for the treatment of pain |
| US8268853B2 (en) | 2009-06-25 | 2012-09-18 | Abbott Laboratories | 3,9-diazaspiro[5,5]undecane amides and ureas and methods of use thereof |
| HUE043522T2 (hu) | 2009-09-04 | 2019-08-28 | Biogen Ma Inc | Bruton tirozinkináz inhibitorok |
| DK3093291T3 (da) | 2009-10-23 | 2019-07-29 | Janssen Pharmaceutica Nv | Disubstituerede octahy-dropyrrolo [3,4-c]pyrroler som orexinreceptormodulatorer |
| JP5848251B2 (ja) * | 2009-10-23 | 2016-01-27 | ヤンセン ファーマシューティカ エヌ．ベー． | オレキシン受容体調節因子としての縮合複素環式化合物 |
| WO2011050200A1 (en) | 2009-10-23 | 2011-04-28 | Janssen Pharmaceutica Nv | Fused heterocyclic compounds as orexin receptor modulators |
| US9586962B2 (en) | 2011-04-20 | 2017-03-07 | Janssen Pharmaceutica Nv | Disubstituted octahydropyrrolo [3,4-C] pyrroles as orexin receptor modulators |
| AR091273A1 (es) | 2012-06-08 | 2015-01-21 | Biogen Idec Inc | Inhibidores de pirimidinil tirosina quinasa |
| KR101655787B1 (ko) | 2014-05-08 | 2016-09-22 | 대우조선해양 주식회사 | 선박의 하이브리드 공기조화시스템 및 그 방법, 그리고 이를 포함하는 선박 또는 해양구조물 |
| KR20160021679A (ko) | 2014-08-18 | 2016-02-26 | 대우조선해양 주식회사 | 극저온 환경의 장비용 히팅장치 및 방법 그리고 이를 구비하는 선박 |
| CN107108597B (zh) | 2014-10-31 | 2020-04-17 | 英立维尔英国有限公司 | 多巴胺d3受体拮抗剂化合物 |
| IL288321B2 (en) | 2016-03-10 | 2025-08-01 | Janssen Pharmaceutica Nv | Methods of treating depression using orexin-2 receptor antagonists |
| EP3487852A1 (en) | 2016-07-21 | 2019-05-29 | Biogen MA Inc. | Succinate forms and compositions of bruton's tyrosine kinase inhibitors |
| WO2019057123A1 (zh) * | 2017-09-20 | 2019-03-28 | 杭州英创医药科技有限公司 | 作为ido抑制剂和/或ido-hdac双重抑制剂的多环化合物 |
| GB201809295D0 (en) | 2018-06-06 | 2018-07-25 | Institute Of Cancer Res Royal Cancer Hospital | Lox inhibitors |
| CR20210240A (es) | 2018-11-14 | 2021-06-08 | Janssen Pharmaceutica Nv | Métodos sintéticos mejorados para elaborar compuestos heterocíclicos fusionados como moduladores del receptor de orexina |
| WO2020239073A1 (zh) * | 2019-05-30 | 2020-12-03 | 中国科学院上海药物研究所 | 一种并环化合物、其制备方法和用途 |
| CN112047878B (zh) * | 2020-10-15 | 2022-04-19 | 郑州猫眼农业科技有限公司 | 4-溴-6-氯吡啶-2-羧酸的制备方法 |
| WO2024189472A1 (en) | 2023-03-14 | 2024-09-19 | Janssen Pharmaceutica Nv | Improved synthetic methods of making substituted pyrimidine intermediates for synthesis of orexin receptor modulators |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59009705D1 (de) * | 1989-04-17 | 1995-11-02 | Bayer Ag | Verfahren zur Herstellung von 2,7-Diazabicyclo(3.3.0)octanen. |
| NL9201810A (nl) | 1992-10-19 | 1994-05-16 | Dsm Nv | Werkwijze voor de omzetting van een olefine of een olefinemengsel. |
| NO301165B1 (no) | 1992-12-25 | 1997-09-22 | Daiichi Seiyaku Co | Bicykliske aminderivater og antibakterielle midler inneholdende disse |
| US5817679A (en) * | 1993-04-01 | 1998-10-06 | University Of Virginia | 7-Azabicyclo 2.2.1!-heptane and -heptene derivatives as cholinergic receptor ligands |
| US5478939A (en) * | 1994-07-20 | 1995-12-26 | American Cyanamid Company | (R,R) and (S,S) 2,5-diazabicyclo [2,2,1]heptane derivatives |
| US5472958A (en) | 1994-08-29 | 1995-12-05 | Abbott Laboratories | 2-((nitro)phenoxymethyl) heterocyclic compounds that enhance cognitive function |
| US5585388A (en) | 1995-04-07 | 1996-12-17 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acetylcholine receptors |
| WO1997005139A1 (en) * | 1995-07-28 | 1997-02-13 | Abbott Laboratories | Furopyridine, thienopyridine, pyrrolopyridine and related pyrimidine, pyridazine and triazine compounds useful in controlling chemical synaptic transmission |
| GB9519558D0 (en) * | 1995-09-26 | 1995-11-29 | Merck Sharp & Dohme | Therapeutic agents |
| JPH09172344A (ja) | 1995-12-19 | 1997-06-30 | Murata Mfg Co Ltd | 圧電共振子 |
| US5733912A (en) | 1997-02-19 | 1998-03-31 | Abbott Laboratories | 7A-heterocycle substituted hexahydro-1H-pyrrolizine compounds useful in controlling chemical synaptic transmission |
| KR100589872B1 (ko) * | 1997-05-30 | 2006-06-15 | 뉴로서치 에이/에스 | 8-아자비사이클로(3,2,1)옥트-2-엔 유도체 및 이의 제조방법 |
| JP2002502383A (ja) * | 1997-05-30 | 2002-01-22 | ニューロサーアチ・アクティーゼルスカブ | ニコチンＡＣｈレセプターに於けるコリン作動性リガンドとしての９−アザビシクロ（３．３．１）ノン−２−エン及びノナン誘導体 |
| GB9722343D0 (en) * | 1997-10-22 | 1997-12-17 | British Telecomm | Distributed virtual environment |
| PL203140B1 (pl) * | 1997-10-27 | 2009-08-31 | Neurosearch As | Pochodna homopiperazyny, kompozycja farmaceutyczna zawierająca te pochodne i zastosowanie tej pochodnej |
| US6632823B1 (en) * | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| DK1068208T3 (da) * | 1998-04-02 | 2003-09-01 | Targacept Inc | Azatricyclo[3.3.1.1]dekanderivater og farmaceutiske sammensætninger, der indeholder dem |
| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| JP2000026408A (ja) | 1998-07-02 | 2000-01-25 | Dai Ichi Seiyaku Co Ltd | 対掌体的に純粋なピロリジン誘導体、その塩、それらの製造方法 |
| US6804251B1 (en) | 1998-11-12 | 2004-10-12 | Broadcom Corporation | System and method for multiplexing data from multiple sources |
| FR2786769B1 (fr) * | 1998-12-04 | 2002-10-25 | Synthelabo | Derives de 2,5-diazabicyclo[2.2.1]heptane, leur preparation et leur application en therapeutique |
| ES2209825T3 (es) * | 1999-01-29 | 2004-07-01 | Abbott Laboratories | Derivados diazabiciclicos utiles como ligandos del receptor nicotinico de la acetilcolina. |
| EP1177196B1 (en) * | 1999-05-04 | 2004-03-10 | Neurosearch A/S | Heteroaryl diazabicycloalkanes, their preparation and use |
| DK1178982T3 (da) * | 1999-05-21 | 2004-11-08 | Abbott Lab | Heterocykliske, substituerede aminoazacykliske forbindelser, der er nyttige som midler til centralnervesystemet |
| ATE289607T1 (de) * | 1999-12-14 | 2005-03-15 | Neurosearch As | Neue heteroaryl-diazabizykloalkane |
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