JP2008531655A5 - - Google Patents
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- Publication number
- JP2008531655A5 JP2008531655A5 JP2007557507A JP2007557507A JP2008531655A5 JP 2008531655 A5 JP2008531655 A5 JP 2008531655A5 JP 2007557507 A JP2007557507 A JP 2007557507A JP 2007557507 A JP2007557507 A JP 2007557507A JP 2008531655 A5 JP2008531655 A5 JP 2008531655A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- ethoxy
- hexahydrophenanthridine
- pyrimidin
- pyridin
- 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
Links
- -1 6-pyrazol-1-yl-pyridin-3-yl Chemical group 0.000 claims 268
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 30
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 30
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 14
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 claims 13
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 12
- SYFJZKLGTLHHLP-DDUZABMNSA-N (2r,4ar,10br)-6-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(N(C)C)N=C1OC SYFJZKLGTLHHLP-DDUZABMNSA-N 0.000 claims 11
- NQMAAFUKIUCXHK-MZMPZRCHSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC NQMAAFUKIUCXHK-MZMPZRCHSA-N 0.000 claims 10
- BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 7
- CMYBBICGMABDIA-SUYBPPKGSA-N (2r,4ar,10br)-6-(2,4-dimethoxypyrimidin-5-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)N=C1OC CMYBBICGMABDIA-SUYBPPKGSA-N 0.000 claims 6
- CMOZXIQDTIORDY-SUYBPPKGSA-N (2r,4ar,10br)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC(OC)=NN=C1OC CMOZXIQDTIORDY-SUYBPPKGSA-N 0.000 claims 6
- ASYQWLQJWUCWAC-XNRPHZJLSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-pyrazin-2-yl-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=CC=N1 ASYQWLQJWUCWAC-XNRPHZJLSA-N 0.000 claims 6
- SHUUGBGBJOERMI-FRFSOERESA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-pyrimidin-5-yl-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=CN=C1 SHUUGBGBJOERMI-FRFSOERESA-N 0.000 claims 6
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 6
- JYJHFMXFMWXCSY-QGPMSJSTSA-N 5-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-1-methylpyridin-2-one Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C=1C=CC(=O)N(C)C=1 JYJHFMXFMWXCSY-QGPMSJSTSA-N 0.000 claims 6
- SYZLBQITYULSFT-FRFSOERESA-N 5-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-1-methylpyrimidin-2-one Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C=1C=NC(=O)N(C)C=1 SYZLBQITYULSFT-FRFSOERESA-N 0.000 claims 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- QEIYBUYALGNLMP-DDUZABMNSA-N (2r,4ar,10br)-6-(4,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C=C1OC QEIYBUYALGNLMP-DDUZABMNSA-N 0.000 claims 4
- BZZHKLFDJXBRDC-QGPMSJSTSA-N (2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 BZZHKLFDJXBRDC-QGPMSJSTSA-N 0.000 claims 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 4
- ZVYSIQCGJMSRRK-FRFSOERESA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methylsulfanylpyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(SC)N=C1 ZVYSIQCGJMSRRK-FRFSOERESA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- JVKGSMLBLUCNGW-ZAJAPVNPSA-N (2R,4aR,10bR)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol (Z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.N([C@H]1[C@H](C[C@H](O)CC1)c1c2cc(c(c1)OCC)OC)=C2c1ccc(OC)nc1OC JVKGSMLBLUCNGW-ZAJAPVNPSA-N 0.000 claims 2
- VEBANIJUYNQNHC-VPSSVJSSSA-N (2R,4aR,10bR)-9-ethoxy-8-methoxy-6-pyrimidin-5-yl-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol (Z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.N([C@H]1[C@H](C[C@H](O)CC1)c1c2cc(c(c1)OCC)OC)=C2c1cncnc1 VEBANIJUYNQNHC-VPSSVJSSSA-N 0.000 claims 2
- SOUMQAJZTFKZLP-VHASUTPUSA-N (2r,4ar,10br)-6-(2,4-dimethoxypyrimidin-5-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)N=C1OC SOUMQAJZTFKZLP-VHASUTPUSA-N 0.000 claims 2
- CZGGSJSPVGHRBC-NSFHIUBZSA-N (2r,4ar,10br)-6-(2,4-dimethoxypyrimidin-5-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2s,3s)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)N=C1OC CZGGSJSPVGHRBC-NSFHIUBZSA-N 0.000 claims 2
- KXCCEPVATZDPGQ-XSUOYMCISA-N (2r,4ar,10br)-6-(2,4-dimethoxypyrimidin-5-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)N=C1OC KXCCEPVATZDPGQ-XSUOYMCISA-N 0.000 claims 2
- DIWPWFPMWFEBCB-VFMMRYQQSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC DIWPWFPMWFEBCB-VFMMRYQQSA-N 0.000 claims 2
- DIWPWFPMWFEBCB-PQJAZPBRSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2s,3s)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC DIWPWFPMWFEBCB-PQJAZPBRSA-N 0.000 claims 2
- JVKGSMLBLUCNGW-SZILIDBSSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC JVKGSMLBLUCNGW-SZILIDBSSA-N 0.000 claims 2
- VGFFPAFLQHSIJQ-ZORIOUSZSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC VGFFPAFLQHSIJQ-ZORIOUSZSA-N 0.000 claims 2
- OJSXWJXECXJZQC-ZORIOUSZSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;hydrobromide Chemical compound Br.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC OJSXWJXECXJZQC-ZORIOUSZSA-N 0.000 claims 2
- ANUPWUDEMSBSCA-ZORIOUSZSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;hydrochloride Chemical compound Cl.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC ANUPWUDEMSBSCA-ZORIOUSZSA-N 0.000 claims 2
- WRKZBAUAJBDJMV-ZORIOUSZSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;oxalic acid Chemical compound OC(=O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC WRKZBAUAJBDJMV-ZORIOUSZSA-N 0.000 claims 2
- BJCPWVIBHCMWNL-VHASUTPUSA-N (2r,4ar,10br)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC(OC)=NN=C1OC BJCPWVIBHCMWNL-VHASUTPUSA-N 0.000 claims 2
- ZELCNKIBPKNMBA-NSFHIUBZSA-N (2r,4ar,10br)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2s,3s)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC(OC)=NN=C1OC ZELCNKIBPKNMBA-NSFHIUBZSA-N 0.000 claims 2
- SFPMTFRVMZMIPQ-XSUOYMCISA-N (2r,4ar,10br)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC(OC)=NN=C1OC SFPMTFRVMZMIPQ-XSUOYMCISA-N 0.000 claims 2
- WFIULHKZYSHDAO-YCLOEFEOSA-N (2r,4ar,10br)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;hydrochloride Chemical compound Cl.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC(OC)=NN=C1OC WFIULHKZYSHDAO-YCLOEFEOSA-N 0.000 claims 2
- SMHWUPMUAQJSKZ-WUKNRWQOSA-N (2r,4ar,10br)-6-(4,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2r)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)CC(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C=C1OC SMHWUPMUAQJSKZ-WUKNRWQOSA-N 0.000 claims 2
- GMXYYOHEMHDTQM-ILQRZEQCSA-N (2r,4ar,10br)-6-(4,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C=C1OC GMXYYOHEMHDTQM-ILQRZEQCSA-N 0.000 claims 2
- WOQGUQZGCOPVHK-DKRTUNLBSA-N (2r,4ar,10br)-6-(4,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2s,3s)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C=C1OC WOQGUQZGCOPVHK-DKRTUNLBSA-N 0.000 claims 2
- DNQTWTJWWGFETG-ZRCLMYKLSA-N (2r,4ar,10br)-6-(4,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;oxalic acid Chemical compound OC(=O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C=C1OC DNQTWTJWWGFETG-ZRCLMYKLSA-N 0.000 claims 2
- JORUIDYXVGOPNX-UQQJPGAFSA-N (2r,4ar,10br)-6-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(N(C)C)N=C1OC JORUIDYXVGOPNX-UQQJPGAFSA-N 0.000 claims 2
- KOZFMOQZJQBOCP-QGPMSJSTSA-N (2r,4ar,10br)-6-[2-(dimethylamino)pyrimidin-5-yl]-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(N(C)C)N=C1 KOZFMOQZJQBOCP-QGPMSJSTSA-N 0.000 claims 2
- KXUADHGNRHKQRL-YVWKXTFCSA-N (2r,4ar,10br)-9-ethoxy-6-(6-imidazol-1-ylpyridin-3-yl)-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C(C=N1)=CC=C1N1C=CN=C1 KXUADHGNRHKQRL-YVWKXTFCSA-N 0.000 claims 2
- GQLSEYHIRYZNNR-FRFSOERESA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methoxypyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)N=C1 GQLSEYHIRYZNNR-FRFSOERESA-N 0.000 claims 2
- WIUHEBBLOCKXMM-QGPMSJSTSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(6-methoxypyridin-3-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol Chemical compound N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1 WIUHEBBLOCKXMM-QGPMSJSTSA-N 0.000 claims 2
- SBMYCALGEFGJOC-ZAIBHORFSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-pyrazin-2-yl-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=CC=N1 SBMYCALGEFGJOC-ZAIBHORFSA-N 0.000 claims 2
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- FVOPPENHGMLJHW-DDUZABMNSA-N [(2r,4ar,10br)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] methanesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(C)(=O)=O)=C1C1=CC(OC)=NN=C1OC FVOPPENHGMLJHW-DDUZABMNSA-N 0.000 claims 2
- RELVPDCWCVLOFZ-OPJGWUQDSA-N [(2r,4ar,10br)-6-(4,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CN=C(OC)C=C1OC RELVPDCWCVLOFZ-OPJGWUQDSA-N 0.000 claims 2
- WDVJDCZCPJKRDJ-QGPMSJSTSA-N [(2r,4ar,10br)-9-ethoxy-8-methoxy-6-pyrimidin-5-yl-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] methanesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(C)(=O)=O)=C1C1=CN=CN=C1 WDVJDCZCPJKRDJ-QGPMSJSTSA-N 0.000 claims 2
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- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- GQEAKQLNHVQDRR-UBQZISFJSA-N (2R,4aR,10bR)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 GQEAKQLNHVQDRR-UBQZISFJSA-N 0.000 claims 1
- WOZYZTAFYKMNNH-JYAGDRSTSA-N (2R,4aR,10bR)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol (2S,3S)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 WOZYZTAFYKMNNH-JYAGDRSTSA-N 0.000 claims 1
- VBRWUGPHRYPPLG-JWYJLEGCSA-N (2R,4aR,10bR)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol (Z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.N([C@H]1[C@H](C[C@H](O)CC1)c1c2cc(c(c1)OCC)OC)=C2c1cnc(OC)c(OC)c1 VBRWUGPHRYPPLG-JWYJLEGCSA-N 0.000 claims 1
- NRLUJUXLESZRHW-ZORIOUSZSA-N (2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1OC NRLUJUXLESZRHW-ZORIOUSZSA-N 0.000 claims 1
- ZELCNKIBPKNMBA-LEOPADSFSA-N (2r,4ar,10br)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC(OC)=NN=C1OC ZELCNKIBPKNMBA-LEOPADSFSA-N 0.000 claims 1
- INDNPAPQWAJHKM-YCLOEFEOSA-N (2r,4ar,10br)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;hydrobromide Chemical compound Br.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC(OC)=NN=C1OC INDNPAPQWAJHKM-YCLOEFEOSA-N 0.000 claims 1
- FNODJHGHHRFDHJ-UQQJPGAFSA-N (2r,4ar,10br)-6-(4,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C=C1OC FNODJHGHHRFDHJ-UQQJPGAFSA-N 0.000 claims 1
- WOZYZTAFYKMNNH-FDBUIAJYSA-N (2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 WOZYZTAFYKMNNH-FDBUIAJYSA-N 0.000 claims 1
- CLTAIKWCBSKALQ-VSLSLIDHSA-N (2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 CLTAIKWCBSKALQ-VSLSLIDHSA-N 0.000 claims 1
- VBRWUGPHRYPPLG-PGMXNCDBSA-N (2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 VBRWUGPHRYPPLG-PGMXNCDBSA-N 0.000 claims 1
- OUCCZDFHUYATJI-AHFLGXKJSA-N (2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 OUCCZDFHUYATJI-AHFLGXKJSA-N 0.000 claims 1
- HNJKXDMXEYEIFE-AHFLGXKJSA-N (2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;hydrochloride Chemical compound Cl.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 HNJKXDMXEYEIFE-AHFLGXKJSA-N 0.000 claims 1
- SVASDVIVCTVCAM-AHFLGXKJSA-N (2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;oxalic acid Chemical compound OC(=O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(OC)C(OC)=C1 SVASDVIVCTVCAM-AHFLGXKJSA-N 0.000 claims 1
- ZCMARMAVCTYDKI-YOLHSKTNSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methylsulfanylpyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(SC)N=C1 ZCMARMAVCTYDKI-YOLHSKTNSA-N 0.000 claims 1
- PZSQTGXCBSIHCA-YOLHSKTNSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methylsulfanylpyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;2-oxopentanedioic acid Chemical compound OC(=O)CCC(=O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(SC)N=C1 PZSQTGXCBSIHCA-YOLHSKTNSA-N 0.000 claims 1
- JQGOVXONTCDCGI-YOLHSKTNSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methylsulfanylpyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;hydrochloride Chemical compound Cl.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(SC)N=C1 JQGOVXONTCDCGI-YOLHSKTNSA-N 0.000 claims 1
- UEMAHGBKFYTBFI-YOLHSKTNSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methylsulfanylpyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;oxalic acid Chemical compound OC(=O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CN=C(SC)N=C1 UEMAHGBKFYTBFI-YOLHSKTNSA-N 0.000 claims 1
- JDRIXRAIWAWZLA-AHFLGXKJSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(6-methoxypyridin-3-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;hydrobromide Chemical compound Br.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1 JDRIXRAIWAWZLA-AHFLGXKJSA-N 0.000 claims 1
- NFQKBFHZCAPBID-AHFLGXKJSA-N (2r,4ar,10br)-9-ethoxy-8-methoxy-6-(6-methoxypyridin-3-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-ol;oxalic acid Chemical compound OC(=O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(OC)N=C1 NFQKBFHZCAPBID-AHFLGXKJSA-N 0.000 claims 1
- CARQFDVHUKDURV-UBQZISFJSA-N 5-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-1-methylpyridin-2-one;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C=1C=CC(=O)N(C)C=1 CARQFDVHUKDURV-UBQZISFJSA-N 0.000 claims 1
- SMEANZSSGBMYNW-YOLHSKTNSA-N 5-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-1-methylpyrimidin-2-one;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C=1C=NC(=O)N(C)C=1 SMEANZSSGBMYNW-YOLHSKTNSA-N 0.000 claims 1
- CPRXJLXJHGXRLI-YOLHSKTNSA-N 5-[(2r,4ar,10br)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-6-yl]-1-methylpyrimidin-2-one;hydrobromide Chemical compound Br.N([C@@H]1CC[C@@H](O)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C=1C=NC(=O)N(C)C=1 CPRXJLXJHGXRLI-YOLHSKTNSA-N 0.000 claims 1
- ZJKXDMABCXIBBC-IDHHARJASA-N 5-[[(2R,4aR,10bR)-6-(3,6-dimethoxypyridazin-4-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl]oxy]-4,5-dioxopentanoic acid Chemical compound O=C(C(=O)O[C@H]1C[C@@H]2C3=CC(=C(C=C3C(=N[C@@H]2CC1)C1=C(N=NC(=C1)OC)OC)OC)OCC)CCC(=O)O ZJKXDMABCXIBBC-IDHHARJASA-N 0.000 claims 1
- MEVWOXSZTJQYHU-XGNWXBCYSA-N Br.C(C)OC1=C(C=C2C(=N[C@@H]3CC[C@H](C[C@@H]3C2=C1)O)C=1C=NC(=CC1)N1C=NC=C1)OC.Br Chemical compound Br.C(C)OC1=C(C=C2C(=N[C@@H]3CC[C@H](C[C@@H]3C2=C1)O)C=1C=NC(=CC1)N1C=NC=C1)OC.Br MEVWOXSZTJQYHU-XGNWXBCYSA-N 0.000 claims 1
- FBKQVBPXRHVJDS-WGKDULJBSA-N Br.C(C)OC1=C(C=C2C(=N[C@@H]3CC[C@H](C[C@@H]3C2=C1)O)C=1C=NC(N(C1)C)=O)OC.Br Chemical compound Br.C(C)OC1=C(C=C2C(=N[C@@H]3CC[C@H](C[C@@H]3C2=C1)O)C=1C=NC(N(C1)C)=O)OC.Br FBKQVBPXRHVJDS-WGKDULJBSA-N 0.000 claims 1
- IHNIVEWIXGQVKQ-SPDSNIDJSA-N Br.COC=1N=NC(=CC1C1=N[C@@H]2CC[C@H](C[C@@H]2C2=CC(=C(C=C12)OC)OCC)O)OC.Br Chemical compound Br.COC=1N=NC(=CC1C1=N[C@@H]2CC[C@H](C[C@@H]2C2=CC(=C(C=C12)OC)OCC)O)OC.Br IHNIVEWIXGQVKQ-SPDSNIDJSA-N 0.000 claims 1
- SOXQMTZHZWKJTM-MLKDPRMFSA-N C(C)OC1=C(C=C2C(=N[C@@H]3CC[C@H](C[C@@H]3C2=C1)O)C=1C=NC(=CC1)OC)OC.C([C@H](O)CC(=O)O)(=O)O Chemical compound C(C)OC1=C(C=C2C(=N[C@@H]3CC[C@H](C[C@@H]3C2=C1)O)C=1C=NC(=CC1)OC)OC.C([C@H](O)CC(=O)O)(=O)O SOXQMTZHZWKJTM-MLKDPRMFSA-N 0.000 claims 1
- RUSOOZAZYKTWIZ-VSLSLIDHSA-N C([C@@H](O)CC(=O)O)(=O)O.C(C)OC1=C(C=C2C(=N[C@@H]3CC[C@H](C[C@@H]3C2=C1)O)C=1C=CC(N(C1)C)=O)OC Chemical compound C([C@@H](O)CC(=O)O)(=O)O.C(C)OC1=C(C=C2C(=N[C@@H]3CC[C@H](C[C@@H]3C2=C1)O)C=1C=CC(N(C1)C)=O)OC RUSOOZAZYKTWIZ-VSLSLIDHSA-N 0.000 claims 1
- ZTPNIMTYRQTDJY-ZBONYCRYSA-N C([C@@H](O)CC(=O)O)(=O)O.COC=1C=C(C=NC1OC)C1=N[C@@H]2CC[C@H](C[C@@H]2C2=CC(=C(C=C12)OC)OCC)O.C([C@H](O)CC(=O)O)(=O)O Chemical compound C([C@@H](O)CC(=O)O)(=O)O.COC=1C=C(C=NC1OC)C1=N[C@@H]2CC[C@H](C[C@@H]2C2=CC(=C(C=C12)OC)OCC)O.C([C@H](O)CC(=O)O)(=O)O ZTPNIMTYRQTDJY-ZBONYCRYSA-N 0.000 claims 1
- BUDCKIQATRLFCY-UHFFFAOYSA-N COC=1C=C(C=NC=1OC)C1C(CCC2N=CC3=CC(=C(C=C3C12)OCC)OC)O Chemical compound COC=1C=C(C=NC=1OC)C1C(CCC2N=CC3=CC(=C(C=C3C12)OCC)OC)O BUDCKIQATRLFCY-UHFFFAOYSA-N 0.000 claims 1
- YRWCXVVQOSRWFS-VPSSVJSSSA-N OC(=O)\C=C/C(O)=O.N([C@H]1[C@H](C[C@H](O)CC1)c1c2cc(c(c1)OCC)OC)=C2c1cnc(SC)nc1 Chemical compound OC(=O)\C=C/C(O)=O.N([C@H]1[C@H](C[C@H](O)CC1)c1c2cc(c(c1)OCC)OC)=C2c1cnc(SC)nc1 YRWCXVVQOSRWFS-VPSSVJSSSA-N 0.000 claims 1
- YQMGDTDBJADPBF-AHFLGXKJSA-N S(=O)(=O)(O)O[C@H]1C[C@@H]2C3=CC(=C(C=C3C(=N[C@@H]2CC1)C=1C=NC(=CC1)OC)OC)OCC.S(=O)(=O)(O)O Chemical compound S(=O)(=O)(O)O[C@H]1C[C@@H]2C3=CC(=C(C=C3C(=N[C@@H]2CC1)C=1C=NC(=CC1)OC)OC)OCC.S(=O)(=O)(O)O YQMGDTDBJADPBF-AHFLGXKJSA-N 0.000 claims 1
- RYZHTPADNPSKKC-QGPMSJSTSA-N [(2R,4aR,10bR)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] hydrogen sulfate Chemical compound S(=O)(=O)(O)O[C@H]1C[C@@H]2C3=CC(=C(C=C3C(=N[C@@H]2CC1)C=1C=NC(=C(C1)OC)OC)OC)OCC RYZHTPADNPSKKC-QGPMSJSTSA-N 0.000 claims 1
- DNHWXVQECCCGSY-MEKIYTOJSA-N [(2r,4ar,10br)-6-(2,4-dimethoxypyrimidin-5-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CN=C(OC)N=C1OC DNHWXVQECCCGSY-MEKIYTOJSA-N 0.000 claims 1
- QLCXSYOGJTURDM-RZPHLTDDSA-N [(2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CC=C(OC)N=C1OC QLCXSYOGJTURDM-RZPHLTDDSA-N 0.000 claims 1
- LVLPROMBBFFSJE-LSBZLQRGSA-N [(2r,4ar,10br)-6-(2,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] methanesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(C)(=O)=O)=C1C1=CC=C(OC)N=C1OC LVLPROMBBFFSJE-LSBZLQRGSA-N 0.000 claims 1
- KDUCXJHIJWAYOI-QFZRFWILSA-N [(2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CN=C(OC)C(OC)=C1 KDUCXJHIJWAYOI-QFZRFWILSA-N 0.000 claims 1
- ANODEILOPNPCCQ-SZVBFZGTSA-N [(2r,4ar,10br)-6-(5,6-dimethoxypyridin-3-yl)-9-ethoxy-8-methoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] methanesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(C)(=O)=O)=C1C1=CN=C(OC)C(OC)=C1 ANODEILOPNPCCQ-SZVBFZGTSA-N 0.000 claims 1
- MEUHHTYZOSBJNN-ZFJSRUIDSA-N [(2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methoxypyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CN=C(OC)N=C1 MEUHHTYZOSBJNN-ZFJSRUIDSA-N 0.000 claims 1
- LNIJNTXPZRSPEN-ZFJSRUIDSA-N [(2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methylsulfanylpyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CN=C(SC)N=C1 LNIJNTXPZRSPEN-ZFJSRUIDSA-N 0.000 claims 1
- SIJHSQKRZSYJQQ-QGPMSJSTSA-N [(2r,4ar,10br)-9-ethoxy-8-methoxy-6-(2-methylsulfanylpyrimidin-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] methanesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(C)(=O)=O)=C1C1=CN=C(SC)N=C1 SIJHSQKRZSYJQQ-QGPMSJSTSA-N 0.000 claims 1
- BJNNATXOLYAMKM-QFZRFWILSA-N [(2r,4ar,10br)-9-ethoxy-8-methoxy-6-(6-methoxypyridin-3-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CC=C(OC)N=C1 BJNNATXOLYAMKM-QFZRFWILSA-N 0.000 claims 1
- KISUKQDRZYMPJO-AVPJRLCVSA-N [(2r,4ar,10br)-9-ethoxy-8-methoxy-6-(6-pyrazol-1-ylpyridin-3-yl)-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C(C=N1)=CC=C1N1C=CC=N1 KISUKQDRZYMPJO-AVPJRLCVSA-N 0.000 claims 1
- HCQPCBHNGBNOPL-JMUQELJHSA-N [(2r,4ar,10br)-9-ethoxy-8-methoxy-6-pyrazin-2-yl-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CN=CC=N1 HCQPCBHNGBNOPL-JMUQELJHSA-N 0.000 claims 1
- KRGRVIHJIBBICS-ZFJSRUIDSA-N [(2r,4ar,10br)-9-ethoxy-8-methoxy-6-pyrimidin-5-yl-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl] 4-methylbenzenesulfonate Chemical compound N([C@@H]1CC[C@H](C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)OS(=O)(=O)C=2C=CC(C)=CC=2)=C1C1=CN=CN=C1 KRGRVIHJIBBICS-ZFJSRUIDSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 239000007909 solid dosage form Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05101619 | 2005-03-02 | ||
| EP05101619.4 | 2005-03-02 | ||
| EP05108442 | 2005-09-14 | ||
| EP05108442.4 | 2005-09-14 | ||
| PCT/EP2006/060377 WO2006092422A1 (en) | 2005-03-02 | 2006-03-01 | Novel salts of 6-heterocyclyl substituted hexahydrophenanthridine derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013241863A Division JP2014040482A (ja) | 2005-03-02 | 2013-11-22 | ６−ヘテロシクリル置換されたヘキサヒドロフェナントリジン誘導体の新規の塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008531655A JP2008531655A (ja) | 2008-08-14 |
| JP2008531655A5 true JP2008531655A5 (https=) | 2009-04-16 |
| JP5478828B2 JP5478828B2 (ja) | 2014-04-23 |
Family
ID=36295528
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007557507A Expired - Fee Related JP5478828B2 (ja) | 2005-03-02 | 2006-03-01 | ６−ヘテロシクリル置換されたヘキサヒドロフェナントリジン誘導体の新規の塩 |
| JP2013241863A Pending JP2014040482A (ja) | 2005-03-02 | 2013-11-22 | ６−ヘテロシクリル置換されたヘキサヒドロフェナントリジン誘導体の新規の塩 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013241863A Pending JP2014040482A (ja) | 2005-03-02 | 2013-11-22 | ６−ヘテロシクリル置換されたヘキサヒドロフェナントリジン誘導体の新規の塩 |
Country Status (24)
| Country | Link |
|---|---|
| US (4) | US7718668B2 (https=) |
| EP (3) | EP2189454B1 (https=) |
| JP (2) | JP5478828B2 (https=) |
| KR (2) | KR101352687B1 (https=) |
| AT (1) | ATE450524T1 (https=) |
| AU (1) | AU2006219867B2 (https=) |
| BR (1) | BRPI0607645A2 (https=) |
| CA (1) | CA2598860C (https=) |
| CY (1) | CY1109753T1 (https=) |
| DE (1) | DE602006010824D1 (https=) |
| DK (1) | DK1856093T3 (https=) |
| EA (1) | EA015376B1 (https=) |
| ES (2) | ES2440590T3 (https=) |
| HR (1) | HRP20100086T1 (https=) |
| IL (2) | IL185276A (https=) |
| ME (1) | ME01172B (https=) |
| MX (1) | MX2007010400A (https=) |
| NO (1) | NO339416B1 (https=) |
| NZ (2) | NZ589278A (https=) |
| PL (1) | PL1856093T3 (https=) |
| PT (1) | PT1856093E (https=) |
| RS (1) | RS51345B (https=) |
| SI (1) | SI1856093T1 (https=) |
| WO (1) | WO2006092422A1 (https=) |
Families Citing this family (11)
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| ATE353217T1 (de) | 2002-08-29 | 2007-02-15 | Altana Pharma Ag | 3-hydroxy-6-phenylphenanthridine als pde-4 inhibitoren |
| CA2556086C (en) | 2004-02-18 | 2014-04-01 | Altana Pharma Ag | Novel guanidinyl-substituted hydroxy-6-phenylphenenthridines as effective phosphodiesterase (pde) 4 inhibitors |
| PL2589599T4 (pl) | 2004-03-03 | 2015-06-30 | Takeda Gmbh | Nowe hydroksy-6-heteroarylofenantrydyny i ich zastosowanie jako inhibitorów PDE4 |
| EP1725534A1 (en) * | 2004-03-10 | 2006-11-29 | Altana Pharma AG | Novel amido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| PL1856093T3 (pl) | 2005-03-02 | 2010-05-31 | Takeda Gmbh | Chlorowodorek (2R,4aR,10bR)-6-(2,6-dimetoksy-pirydyn-3-ylo)-9-etoksy-8-metoksy-1,2,3,4,4a,10b-heksahydrofenantrydyn-2-olu |
| WO2008028914A1 (en) | 2006-09-07 | 2008-03-13 | Nycomed Gmbh | Combination treatment for diabetes mellitus |
| WO2009109525A1 (en) * | 2008-03-03 | 2009-09-11 | Nycomed Gmbh | Use of a specific pde4 inhibitor for the treatment and/or prophylaxis of non-alcoholic fatty liver disease |
| MX375348B (es) | 2011-12-15 | 2025-03-06 | Alkermes Pharma Ireland Ltd | Composiciones de la buprenorfina y antagonistas de los receptores opioide-mu. |
| WO2015110394A1 (en) | 2014-01-22 | 2015-07-30 | Takeda Gmbh | Treatment of partly controlled or uncontrolled severe asthma with a pde4 inhibitor (and in combination with a leukotriene modifier) |
| WO2018037109A1 (en) | 2016-08-26 | 2018-03-01 | Takeda Gmbh | Treatment of nonalcoholic fatty liver disease |
| JP2020510071A (ja) | 2017-03-16 | 2020-04-02 | タケダ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 特発性肺線維症の治療 |
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| GB9027055D0 (en) | 1990-12-13 | 1991-02-06 | Sandoz Ltd | Organic compounds |
| AU650953B2 (en) * | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| BR9707233A (pt) | 1996-01-31 | 1999-07-20 | Byk Gulden Lomberg Chem Fab | Fenantridinas |
| SI0889886T1 (en) | 1996-03-26 | 2003-02-28 | Altana Pharma Ag | Novel phenanthridines substituted in the 6 position |
| US6127378A (en) | 1996-03-26 | 2000-10-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridines substituted in the 6 position |
| PL189641B1 (pl) | 1996-11-11 | 2005-09-30 | Altana Pharma Ag | Benzonaftyrydyny, środki farmaceutyczne je zawierające oraz zastosowanie benzonaftyrydyn |
| SI0968211T1 (en) | 1997-03-07 | 2004-02-29 | Altana Pharma Ag | Tetrazole derivatives |
| ES2193539T3 (es) | 1997-06-03 | 2003-11-01 | Altana Pharma Ag | Benzonaftiridinas. |
| WO1999005112A1 (en) | 1997-07-25 | 1999-02-04 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituted 6-alkylphenanthridines |
| JP2001510827A (ja) | 1997-07-25 | 2001-08-07 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 置換６−フェニルフェナントリジン |
| PT998460E (pt) | 1997-07-25 | 2004-07-30 | Altana Pharma Ag | Novos derivados de tetrazole |
| DK1075477T3 (da) | 1998-05-05 | 2003-06-30 | Altana Pharma Ag | Nye benzonaphthyridin-N-oxider |
| AU5970199A (en) | 1998-08-31 | 2000-03-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzonaphthyridine-n-oxides comprising a pde3 and pde4 inhibiting activity |
| TR200501553T2 (tr) | 1999-01-15 | 2005-06-21 | Altana Pharma Ag | PDE-IV inhibe edici aktivitesi olan fenilfenantridinler |
| WO2000042019A1 (en) | 1999-01-15 | 2000-07-20 | Byk Gulden Lomberg Chemische Fabrik Gmbh | 6-arylphenanthridines with pde-iv inhibiting activity |
| DE60020079T2 (de) | 1999-01-15 | 2006-01-19 | Altana Pharma Ag | Phenanthridin-N-oxide mit PDE-IV-hemmender Wirkung |
| ES2241571T3 (es) | 1999-01-15 | 2005-11-01 | Altana Pharma Ag | N-oxidos de fenantrinida con actividad inhividora de pde-iv. |
| CA2360386A1 (en) | 1999-01-15 | 2000-07-20 | Beate Gutterer | Polysubstituted 6-phenylphenanthridines with pde-iv inhibiting activity |
| WO2001051470A1 (en) | 2000-01-11 | 2001-07-19 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridine-n-oxides |
| DE60125026T2 (de) | 2000-03-23 | 2007-06-28 | Takeda Pharmaceutical Co. Ltd. | Fluorisochinolinderivate, verfahren zu ihrer herstellung und ihre anwendung |
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| WO2002005616A1 (en) * | 2000-07-14 | 2002-01-24 | Altana Pharma Ag | Novel 6-phenylphenanthridines |
| WO2002006238A1 (en) | 2000-07-14 | 2002-01-24 | Altana Pharma Ag | Cycloalkyl - or cycloalkylmethyl-substituted 6-phenylphenanthridines |
| US6936622B2 (en) | 2001-02-21 | 2005-08-30 | Altana Pharma Ag | 6-phenylbenzonaphthyridines |
| CA2495597A1 (en) | 2002-08-17 | 2004-03-04 | Altana Pharma Ag | Novel phenanthridines |
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| ATE353217T1 (de) | 2002-08-29 | 2007-02-15 | Altana Pharma Ag | 3-hydroxy-6-phenylphenanthridine als pde-4 inhibitoren |
| JP4587294B2 (ja) | 2002-08-29 | 2010-11-24 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｐｄｅ４インヒビターとしての２−ヒドロキシ−６−フェニルフェナントリジン |
| CA2556086C (en) | 2004-02-18 | 2014-04-01 | Altana Pharma Ag | Novel guanidinyl-substituted hydroxy-6-phenylphenenthridines as effective phosphodiesterase (pde) 4 inhibitors |
| AR049419A1 (es) | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| PL2589599T4 (pl) * | 2004-03-03 | 2015-06-30 | Takeda Gmbh | Nowe hydroksy-6-heteroarylofenantrydyny i ich zastosowanie jako inhibitorów PDE4 |
| AU2005220034A1 (en) | 2004-03-09 | 2005-09-15 | Nycomed Gmbh | Novel isoamido-substituted hydroxy-6-phenylphenanthridines and their use as PDE4 inhibitors |
| WO2005085203A1 (en) | 2004-03-10 | 2005-09-15 | Altana Pharma Ag | Novel difluoroethoxy-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| EP1725534A1 (en) | 2004-03-10 | 2006-11-29 | Altana Pharma AG | Novel amido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| CA2558390A1 (en) | 2004-03-10 | 2005-09-22 | Altana Pharma Ag | Novel thio-containing hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| PL1856093T3 (pl) | 2005-03-02 | 2010-05-31 | Takeda Gmbh | Chlorowodorek (2R,4aR,10bR)-6-(2,6-dimetoksy-pirydyn-3-ylo)-9-etoksy-8-metoksy-1,2,3,4,4a,10b-heksahydrofenantrydyn-2-olu |
-
2006
- 2006-03-01 PL PL06708593T patent/PL1856093T3/pl unknown
- 2006-03-01 PT PT06708593T patent/PT1856093E/pt unknown
- 2006-03-01 DK DK06708593.6T patent/DK1856093T3/da active
- 2006-03-01 EA EA200701817A patent/EA015376B1/ru not_active IP Right Cessation
- 2006-03-01 AU AU2006219867A patent/AU2006219867B2/en not_active Ceased
- 2006-03-01 KR KR1020077021911A patent/KR101352687B1/ko not_active Expired - Fee Related
- 2006-03-01 EP EP09176620.4A patent/EP2189454B1/en not_active Expired - Lifetime
- 2006-03-01 WO PCT/EP2006/060377 patent/WO2006092422A1/en not_active Ceased
- 2006-03-01 HR HR20100086T patent/HRP20100086T1/hr unknown
- 2006-03-01 CA CA2598860A patent/CA2598860C/en not_active Expired - Fee Related
- 2006-03-01 AT AT06708593T patent/ATE450524T1/de active
- 2006-03-01 ME MEP-2010-34A patent/ME01172B/me unknown
- 2006-03-01 NZ NZ589278A patent/NZ589278A/en not_active IP Right Cessation
- 2006-03-01 SI SI200630567T patent/SI1856093T1/sl unknown
- 2006-03-01 US US11/884,934 patent/US7718668B2/en not_active Expired - Fee Related
- 2006-03-01 DE DE602006010824T patent/DE602006010824D1/de not_active Expired - Lifetime
- 2006-03-01 BR BRPI0607645-9A patent/BRPI0607645A2/pt not_active Application Discontinuation
- 2006-03-01 RS RSP-2010/0073A patent/RS51345B/sr unknown
- 2006-03-01 MX MX2007010400A patent/MX2007010400A/es active IP Right Grant
- 2006-03-01 EP EP10177835.5A patent/EP2295423B1/en not_active Expired - Lifetime
- 2006-03-01 EP EP06708593A patent/EP1856093B1/en not_active Expired - Lifetime
- 2006-03-01 KR KR1020137022101A patent/KR101421914B1/ko not_active Expired - Fee Related
- 2006-03-01 NZ NZ560268A patent/NZ560268A/en not_active IP Right Cessation
- 2006-03-01 ES ES10177835.5T patent/ES2440590T3/es not_active Expired - Lifetime
- 2006-03-01 JP JP2007557507A patent/JP5478828B2/ja not_active Expired - Fee Related
- 2006-03-01 ES ES06708593T patent/ES2337083T3/es not_active Expired - Lifetime
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2007
- 2007-08-14 IL IL185276A patent/IL185276A/en not_active IP Right Cessation
- 2007-09-24 NO NO20074843A patent/NO339416B1/no not_active IP Right Cessation
-
2010
- 2010-01-27 CY CY20101100081T patent/CY1109753T1/el unknown
- 2010-03-26 US US12/659,977 patent/US8354535B2/en not_active Expired - Fee Related
-
2012
- 2012-12-07 US US13/707,969 patent/US8754218B2/en not_active Expired - Fee Related
-
2013
- 2013-07-21 IL IL227565A patent/IL227565A/en not_active IP Right Cessation
- 2013-10-11 US US14/051,835 patent/US8829189B2/en not_active Expired - Fee Related
- 2013-11-22 JP JP2013241863A patent/JP2014040482A/ja active Pending
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