JP4145492B2 - テトラヒドロピリドエーテル - Google Patents
テトラヒドロピリドエーテル Download PDFInfo
- Publication number
- JP4145492B2 JP4145492B2 JP2000574109A JP2000574109A JP4145492B2 JP 4145492 B2 JP4145492 B2 JP 4145492B2 JP 2000574109 A JP2000574109 A JP 2000574109A JP 2000574109 A JP2000574109 A JP 2000574109A JP 4145492 B2 JP4145492 B2 JP 4145492B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- dimethyl
- imidazo
- phenyl
- naphthyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- PWILYDZRJORZDR-MISYRCLQSA-N (7r,8r,9r)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-MISYRCLQSA-N 0.000 claims abstract description 3
- -1 hydroxy, methoxy, ethoxy, isopropoxy, methoxyethoxy Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000008177 pharmaceutical agent Substances 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- PFUDJBXGGYVENA-BHIYHBOVSA-N (7r,8r,9r)-7,8-dimethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine Chemical compound C1([C@@H]2[C@H]([C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)OC)=CC=CC=C1 PFUDJBXGGYVENA-BHIYHBOVSA-N 0.000 claims description 2
- RJASEHFHFJEXPR-BHIYHBOVSA-N (7r,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-BHIYHBOVSA-N 0.000 claims description 2
- GDQBYAHOQAFREY-KBAYOESNSA-N (7r,8r,9r)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-KBAYOESNSA-N 0.000 claims description 2
- PWILYDZRJORZDR-YSIASYRMSA-N (7r,8s,9s)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-YSIASYRMSA-N 0.000 claims description 2
- GDQBYAHOQAFREY-RYQLBKOJSA-N (7r,8s,9s)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-RYQLBKOJSA-N 0.000 claims description 2
- LHJMQBVQSCNUMD-RLLQIKCJSA-N (7s,8r,9r)-2,3-dimethyl-9-phenyl-7-propan-2-yloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC(C)C)=CC=CC=C1 LHJMQBVQSCNUMD-RLLQIKCJSA-N 0.000 claims description 2
- PWILYDZRJORZDR-RLLQIKCJSA-N (7s,8r,9r)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-RLLQIKCJSA-N 0.000 claims description 2
- RJASEHFHFJEXPR-QRQLOZEOSA-N (7s,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-QRQLOZEOSA-N 0.000 claims description 2
- GDQBYAHOQAFREY-NXHRZFHOSA-N (7s,8r,9r)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-NXHRZFHOSA-N 0.000 claims description 2
- PWILYDZRJORZDR-IHPCNDPISA-N (7s,8s,9s)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-IHPCNDPISA-N 0.000 claims description 2
- GDQBYAHOQAFREY-SZMVWBNQSA-N (7s,8s,9s)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-SZMVWBNQSA-N 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 210000004211 gastric acid Anatomy 0.000 abstract description 3
- 230000028327 secretion Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FHHGNULEXOWEKU-DJIMGWMZSA-N (7r,8r,9r)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine-7,8-diol Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3[C@@H](O)[C@@H]2O)C)C)=CC=CC=C1 FHHGNULEXOWEKU-DJIMGWMZSA-N 0.000 description 3
- PIKFXKSSNMLKLP-UHFFFAOYSA-N 1,2,3,5-tetrahydroimidazo[1,2-h][1,7]naphthyridine Chemical compound C1C=C2C=CC=NC2=C2N1CCN2 PIKFXKSSNMLKLP-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FHHGNULEXOWEKU-XIRDDKMYSA-N C1([C@@H]2NC=3C4=NC(=C(N4C=CC=3[C@H](O)[C@H]2O)C)C)=CC=CC=C1 Chemical compound C1([C@@H]2NC=3C4=NC(=C(N4C=CC=3[C@H](O)[C@H]2O)C)C)=CC=CC=C1 FHHGNULEXOWEKU-XIRDDKMYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 108010079943 Pentagastrin Proteins 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000000812 cholinergic antagonist Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 3
- 229960000444 pentagastrin Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HZARBZKYLFMYGP-RHSMWYFYSA-N (8r,9r)-8-hydroxy-2,3-dimethyl-9-phenyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3C(=O)[C@@H]2O)C)C)=CC=CC=C1 HZARBZKYLFMYGP-RHSMWYFYSA-N 0.000 description 2
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 230000009858 acid secretion Effects 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 229960002626 clarithromycin Drugs 0.000 description 2
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- LKQXJYDAALZCAF-UHFFFAOYSA-N imidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CN2C=CN=C12 LKQXJYDAALZCAF-UHFFFAOYSA-N 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229960000282 metronidazole Drugs 0.000 description 2
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 210000001187 pylorus Anatomy 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- FHHGNULEXOWEKU-HYVNUMGLSA-N (7s,8r,9r)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine-7,8-diol Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3[C@H](O)[C@@H]2O)C)C)=CC=CC=C1 FHHGNULEXOWEKU-HYVNUMGLSA-N 0.000 description 1
- HZARBZKYLFMYGP-YOEHRIQHSA-N (8s,9s)-8-hydroxy-2,3-dimethyl-9-phenyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1([C@@H]2NC=3C4=NC(=C(N4C=CC=3C(=O)[C@H]2O)C)C)=CC=CC=C1 HZARBZKYLFMYGP-YOEHRIQHSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- VSWPGAIWKHPTKX-UHFFFAOYSA-N 1-methyl-10-[2-(4-methyl-1-piperazinyl)-1-oxoethyl]-5H-thieno[3,4-b][1,5]benzodiazepin-4-one Chemical compound C1CN(C)CCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=CSC(C)=C21 VSWPGAIWKHPTKX-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
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- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- General Health & Medical Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Rheumatology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843504 | 1998-09-23 | ||
| EP19843504.5 | 1998-09-23 | ||
| EP98117988 | 1998-09-23 | ||
| EP98117988.0 | 1998-09-23 | ||
| PCT/EP1999/006899 WO2000017200A1 (en) | 1998-09-23 | 1999-09-17 | Tetrahydropyridoethers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002526499A JP2002526499A (ja) | 2002-08-20 |
| JP2002526499A5 JP2002526499A5 (cg-RX-API-DMAC7.html) | 2005-11-17 |
| JP4145492B2 true JP4145492B2 (ja) | 2008-09-03 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000574109A Expired - Lifetime JP4145492B2 (ja) | 1998-09-23 | 1999-09-17 | テトラヒドロピリドエーテル |
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Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ292335B6 (cs) | 1998-09-23 | 2003-09-17 | Altana Pharma Ag | Tetrahydropyridoethery, jejich použití a farmaceutický prostředek |
| US6503923B1 (en) | 1999-04-17 | 2003-01-07 | Altana Pharma Ag | Haloalkoxy imidazonaphthyridines |
| CA2285516C (en) * | 1999-05-12 | 2010-12-07 | President And Fellows Of Harvard College | Dopamine transporter imaging agents |
| MXPA02009549A (es) * | 2000-03-29 | 2004-05-14 | Altana Pharma Ag | Imidazopiridinas triciclicas. |
| ATE311389T1 (de) * | 2000-03-29 | 2005-12-15 | Altana Pharma Ag | Wirkstoffvorläufer von imidazopyridin-derivaten |
| CN1692113A (zh) * | 2000-10-25 | 2005-11-02 | 奥坦纳医药公司 | 作为胃分泌抑制剂的多取代咪唑并吡啶 |
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| WO2002069968A1 (en) * | 2001-03-08 | 2002-09-12 | Astrazeneca Ab | New use |
| EP1414821B1 (en) | 2001-08-02 | 2006-08-16 | ALTANA Pharma AG | Tricyclic epoxides |
| CN1656096A (zh) * | 2001-08-03 | 2005-08-17 | 奥坦纳医药公司 | 用于治疗胃肠病症的烷基－取代的咪唑吡啶 |
| WO2003014120A1 (en) * | 2001-08-03 | 2003-02-20 | Altana Pharma Ag | Amino-substituted imidazopyridines for the treatment of gastrointestinal diseases |
| EP1476445A1 (en) | 2002-02-15 | 2004-11-17 | ALTANA Pharma AG | Tricyclic n-acyl compounds |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| AU2003227710A1 (en) * | 2002-05-07 | 2003-11-11 | Altana Pharma Ag | New combination of reversible proton pump inhibitors and airway therapeutics for treating airway disorders |
| MXPA05005117A (es) | 2002-11-19 | 2005-07-01 | Altana Pharma Ag | Imidazopiridinas 8-sustituidas. |
| US7879833B2 (en) | 2002-12-12 | 2011-02-01 | Nycomed Gmbh | Combination medicament |
| KR20050088176A (ko) * | 2002-12-20 | 2005-09-02 | 알타나 파마 아게 | 8-트리알킬실록시-2-메틸-9-페닐-7-옥소-7,8,9,10-테트라히드로이미다조[1,2-ｈ][1,7]나프티리딘 |
| EP1599175A2 (en) * | 2003-02-17 | 2005-11-30 | ALTANA Pharma AG | Imidazopyridines containing combinations and their use in treating gastrointestinal inflammatory disorders |
| MXPA04008070A (es) | 2003-03-10 | 2004-11-26 | Altana Pharma Ag | Novedoso proceso para la preparacion de roflumilasto. |
| TW200503783A (en) * | 2003-04-11 | 2005-02-01 | Altana Pharma Ag | Oral pharmaceutical preparation for proton pump antagonists |
| SA04250092B1 (ar) * | 2003-05-14 | 2008-05-04 | التانا فاروا ايه جي | مركب وسيط جديد لتحضير مركبات إيميدازوبيريدين imidazopyridines فعالة علاجياً |
| WO2004105795A1 (en) * | 2003-05-27 | 2004-12-09 | Altana Pharma Ag | Pharmaceutical combinations of a proton pump inhibitor and a compound which modifies gastrointestinal motility |
| AU2004268641A1 (en) * | 2003-08-29 | 2005-03-10 | Dynogen Pharmaceuticals, Inc. | Compositions useful for treating gastrointestinal motility disorders |
| ES2452691T5 (es) | 2003-09-16 | 2022-09-14 | Covis Pharma Gmbh | Uso de ciclesonida para el tratamiento de enfermedades respiratorias |
| EP1974730A1 (en) | 2003-11-03 | 2008-10-01 | AstraZeneca AB | Imidazo[1,2-a]pyridine derivatives for use in the treatment of sleep disturbance due to silent gastro-esophageal reflux |
| AU2004298453A1 (en) | 2003-12-19 | 2005-06-30 | Altana Pharma Ag | Intermediates for the preparation of tricyclic dihydropyrano -imidazo -pyridines derivatives |
| NZ549011A (en) * | 2004-02-17 | 2009-04-30 | Altana Pharma Ag | Tricyclic imidazopyridines and intermediates for the synthesis thereof |
| PL1784404T3 (pl) | 2004-09-03 | 2012-04-30 | Yuhan Corp | Pochodne pirolo[2,3-c]pirydyny i sposoby ich wytwarzania |
| EP1784403B1 (en) | 2004-09-03 | 2013-07-17 | Yuhan Corporation | Pyrrolo[3,2-b]pyridine derivatives and processes for the preparation thereof |
| US8148529B2 (en) | 2004-09-03 | 2012-04-03 | Yuhan Corporation | Pyrrolo[3,2-C] pyridine derivatives and processes for the preparation thereof |
| JP5383183B2 (ja) * | 2005-03-16 | 2014-01-08 | 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 | ロフルミラストを含有する矯味された剤形 |
| EP2080513A1 (en) | 2008-01-16 | 2009-07-22 | Schraermeyer, Ulrich, Prof. Dr. rer. nat | Tetrahydropyridoethers for treatment of AMD |
| WO2011004882A1 (ja) * | 2009-07-09 | 2011-01-13 | ラクオリア創薬株式会社 | 消化管運動異常が関与する疾患を治療するためのアシッドポンプ拮抗剤 |
| WO2012027240A1 (en) * | 2010-08-23 | 2012-03-01 | Schering Corporation | Fused tricyclic inhibitors of mammalian target of rapamycin |
| KR101699145B1 (ko) * | 2012-06-15 | 2017-02-03 | (주)바이오팜솔루션즈 | 페닐알킬설파메이트 화합물 및 이를 포함하는 근육 이완제 조성물 |
| EP3054949A1 (en) | 2013-10-08 | 2016-08-17 | Katairo GmbH | Tetrahydropyridoethers for the treatment of stargardt's disease |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4468400A (en) * | 1982-12-20 | 1984-08-28 | Schering Corporation | Antiulcer tricyclic imidazo [1,2-a]pyridines |
| DE3855692D1 (de) | 1987-07-16 | 1997-01-16 | Byk Gulden Lomberg Chem Fab | Imidazo[1,2-a]pyridine |
| SE9401197D0 (sv) * | 1994-04-11 | 1994-04-11 | Astra Ab | Active compounds |
| AU702166B2 (en) * | 1994-07-28 | 1999-02-18 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Acylimidazopyridines |
| WO1998042707A1 (en) * | 1997-03-24 | 1998-10-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyrido compounds |
| CU23088A3 (es) * | 1997-03-24 | 2005-10-19 | Altana Pharma Ag | Compuestos de tetra-hidropiridina. |
| CZ292335B6 (cs) | 1998-09-23 | 2003-09-17 | Altana Pharma Ag | Tetrahydropyridoethery, jejich použití a farmaceutický prostředek |
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1999
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- 1999-09-17 DE DE69905178T patent/DE69905178T2/de not_active Expired - Lifetime
- 1999-09-17 CN CNB998112992A patent/CN1155598C/zh not_active Expired - Fee Related
- 1999-09-17 KR KR1020017003553A patent/KR100668400B1/ko not_active Expired - Fee Related
- 1999-09-17 ID IDW20010682A patent/ID28896A/id unknown
- 1999-09-17 CN CNB2004100384351A patent/CN100506821C/zh not_active Expired - Fee Related
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- 1999-09-17 AU AU61920/99A patent/AU763463B2/en not_active Expired
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- 1999-09-17 WO PCT/EP1999/006899 patent/WO2000017200A1/en not_active Ceased
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- 1999-09-17 CA CA002344251A patent/CA2344251A1/en not_active Abandoned
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- 1999-09-17 SK SK399-2001A patent/SK285165B6/sk not_active IP Right Cessation
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