NO314084B1 - Tetrahydropyridforbindelser - Google Patents
Tetrahydropyridforbindelser Download PDFInfo
- Publication number
- NO314084B1 NO314084B1 NO19994584A NO994584A NO314084B1 NO 314084 B1 NO314084 B1 NO 314084B1 NO 19994584 A NO19994584 A NO 19994584A NO 994584 A NO994584 A NO 994584A NO 314084 B1 NO314084 B1 NO 314084B1
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- dimethyl
- alkyl
- tetrahydroimidazo
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 3
- 230000002265 prevention Effects 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- NRDLPGJVHWGQCG-RHSMWYFYSA-N (8r,9r)-8-hydroxy-2-methyl-7-oxo-9-phenyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridine-3-carbaldehyde Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3C(=O)[C@@H]2O)C=O)C)=CC=CC=C1 NRDLPGJVHWGQCG-RHSMWYFYSA-N 0.000 claims description 3
- XFZUUVDSWPBDJF-UHFFFAOYSA-N 2,3-dimethyl-9-[2-(trifluoromethyl)phenyl]-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1C(=O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=CC=CC=C1C(F)(F)F XFZUUVDSWPBDJF-UHFFFAOYSA-N 0.000 claims description 3
- FCIWOTAANUDCRC-UHFFFAOYSA-N 2,3-dimethyl-9-phenyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1C(=O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=CC=CC=C1 FCIWOTAANUDCRC-UHFFFAOYSA-N 0.000 claims description 3
- HZARBZKYLFMYGP-UHFFFAOYSA-N 8-hydroxy-2,3-dimethyl-9-phenyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound OC1C(=O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=CC=CC=C1 HZARBZKYLFMYGP-UHFFFAOYSA-N 0.000 claims description 3
- JXQIJESUJOCBOF-UHFFFAOYSA-N 9-(2,6-dichlorophenyl)-2,3-dimethyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1C(=O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=C(Cl)C=CC=C1Cl JXQIJESUJOCBOF-UHFFFAOYSA-N 0.000 claims description 3
- HFOHVUUXYKVSBA-UHFFFAOYSA-N 9-(2-chlorophenyl)-2,3-dimethyl-9,10-dihydro-8h-imidazo[1,2-h][1,7]naphthyridin-7-one Chemical compound C1C(=O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=CC=CC=C1Cl HFOHVUUXYKVSBA-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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 claims 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 claims description 2
- UARVGCSOELRCJC-UHFFFAOYSA-N 2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-ol Chemical compound C1C(O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=CC=CC=C1 UARVGCSOELRCJC-UHFFFAOYSA-N 0.000 claims description 2
- FHHGNULEXOWEKU-UHFFFAOYSA-N 2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine-7,8-diol Chemical compound OC1C(O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=CC=CC=C1 FHHGNULEXOWEKU-UHFFFAOYSA-N 0.000 claims description 2
- CLCJITJMWJHMLB-UHFFFAOYSA-N 9-(2,6-dichlorophenyl)-2,3-dimethyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-ol Chemical compound C1C(O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=C(Cl)C=CC=C1Cl CLCJITJMWJHMLB-UHFFFAOYSA-N 0.000 claims description 2
- MPLVNHBAZKUUQD-UHFFFAOYSA-N 9-(2-chlorophenyl)-2,3-dimethyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-ol Chemical compound C1C(O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=CC=CC=C1Cl MPLVNHBAZKUUQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- RXJLYUDZPYXONU-DJIMGWMZSA-N (7r,8r,9r)-3-(hydroxymethyl)-2-methyl-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)CO)C)=CC=CC=C1 RXJLYUDZPYXONU-DJIMGWMZSA-N 0.000 claims 1
- RJEMRAAECBKWRL-UHFFFAOYSA-N 2,3-dimethyl-9-[2-(trifluoromethyl)phenyl]-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-ol Chemical compound C1C(O)C=2C=CN3C(C)=C(C)N=C3C=2NC1C1=CC=CC=C1C(F)(F)F RJEMRAAECBKWRL-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- -1 ethylenedioxy radical Chemical class 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 210000002784 stomach Anatomy 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 125000000468 ketone group Chemical group 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 5
- 229960001701 chloroform Drugs 0.000 description 5
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- 230000002496 gastric effect Effects 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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 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
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 108010079943 Pentagastrin Proteins 0.000 description 3
- 208000007107 Stomach Ulcer Diseases 0.000 description 3
- 150000007513 acids Chemical class 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
- 238000001035 drying Methods 0.000 description 3
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- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 239000012044 organic layer Substances 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
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- 238000011321 prophylaxis Methods 0.000 description 3
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
- 229960004633 pirenzepine Drugs 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- BZGIPVGCJGXQTA-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] n,n-diphenylcarbamothioate Chemical compound C=1C=CC=CC=1N(C(=O)SCCN(CC)CC)C1=CC=CC=C1 BZGIPVGCJGXQTA-UHFFFAOYSA-N 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 208000018556 stomach disease Diseases 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229950004351 telenzepine Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97104961 | 1997-03-24 | ||
| DE19747929 | 1997-10-30 | ||
| PCT/EP1998/001615 WO1998042707A1 (en) | 1997-03-24 | 1998-03-19 | Tetrahydropyrido compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO994584D0 NO994584D0 (no) | 1999-09-21 |
| NO994584L NO994584L (no) | 1999-11-23 |
| NO314084B1 true NO314084B1 (no) | 2003-01-27 |
Family
ID=26041204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19994584A NO314084B1 (no) | 1997-03-24 | 1999-09-21 | Tetrahydropyridforbindelser |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6197783B1 (cs) |
| JP (1) | JP4138022B2 (cs) |
| KR (1) | KR100523422B1 (cs) |
| CN (2) | CN1250546C (cs) |
| AT (1) | ATE265455T1 (cs) |
| AU (1) | AU740578B2 (cs) |
| BG (1) | BG64157B1 (cs) |
| BR (1) | BR9807883A (cs) |
| CA (1) | CA2284747A1 (cs) |
| CU (1) | CU23088A3 (cs) |
| CY (1) | CY2538B1 (cs) |
| CZ (1) | CZ290548B6 (cs) |
| DE (1) | DE69823493T2 (cs) |
| DK (1) | DK0971922T3 (cs) |
| EA (1) | EA002402B1 (cs) |
| EE (1) | EE03771B1 (cs) |
| ES (1) | ES2219890T3 (cs) |
| HK (1) | HK1067365A1 (cs) |
| ID (1) | ID22718A (cs) |
| IL (1) | IL131407A0 (cs) |
| IS (1) | IS2077B (cs) |
| NO (1) | NO314084B1 (cs) |
| NZ (1) | NZ337325A (cs) |
| PL (1) | PL190803B1 (cs) |
| PT (1) | PT971922E (cs) |
| RS (1) | RS49617B (cs) |
| SI (1) | SI0971922T1 (cs) |
| SK (1) | SK283288B6 (cs) |
| TR (1) | TR199902257T2 (cs) |
| UA (1) | UA61102C2 (cs) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR200100805T2 (tr) * | 1998-09-23 | 2001-08-21 | Byk Gulden Lomberg Chemische Fabr�K Gmbh | Tetrahidropiridoeterler |
| DE69938192D1 (en) * | 1998-11-03 | 2008-04-03 | Nycomed Gmbh | Imidazonaphthyridine |
| DE10001037C1 (de) * | 2000-01-13 | 2001-12-13 | Byk Gulden Lomberg Chem Fab | Verfahren und Zwischenprodukte zur Herstellung von Imidazopyridinen |
| CA2404477A1 (en) * | 2000-03-29 | 2001-10-04 | Altana Pharma Ag | Tricyclic imidazopyridines |
| CZ20023116A3 (cs) * | 2000-03-29 | 2003-01-15 | Altana Pharma Ag | Alkylované imidazopyridinové sloučeniny |
| SK286850B6 (sk) * | 2000-03-29 | 2009-06-05 | Altana Pharma Ag | Prekurzory imidazopyridínových derivátov, farmaceutický prostriedok s ich obsahom a ich použitie |
| EP1332143A1 (en) * | 2000-10-25 | 2003-08-06 | ALTANA Pharma AG | Polysubstituted imidazopyridines as gastric secretion inhibitors |
| IL159554A0 (en) * | 2001-08-10 | 2004-06-01 | Altana Pharma Ag | Tricyclic imidazopyridine derivatives and pharmaceutical compositions containing the same |
| PL375567A1 (en) * | 2002-11-19 | 2005-11-28 | Altana Pharma Ag | 8-substituted imidazopyridines |
| TW200503783A (en) * | 2003-04-11 | 2005-02-01 | Altana Pharma Ag | Oral pharmaceutical preparation for proton pump antagonists |
| US7662821B2 (en) | 2003-10-08 | 2010-02-16 | Bayer Schering Pharma Ag | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
| WO2005034939A1 (de) * | 2003-10-08 | 2005-04-21 | Schering Aktiengesellschaft | Tetrahydronaphthalinderivate, verfahren zu ihrer herstellung und ihre verwendung als entzündungshemmer |
| US7638515B2 (en) * | 2003-10-08 | 2009-12-29 | Bayer Schering Pharma Aktiengesellschaft | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
| US20080153859A1 (en) * | 2004-04-05 | 2008-06-26 | Hartmut Rehwinkel | Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
| US20060084652A1 (en) * | 2004-09-09 | 2006-04-20 | Stefan Baeurle | Alkylidene-tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
| US20060229305A1 (en) * | 2005-03-22 | 2006-10-12 | Markus Berger | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
| EP1834948A1 (de) * | 2006-03-15 | 2007-09-19 | Bayer Schering Pharma Aktiengesellschaft | Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
Family Cites Families (3)
| 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 |
| JP2656101B2 (ja) | 1987-07-16 | 1997-09-24 | 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 | 新規ジアゾール |
| IL108520A (en) * | 1993-02-15 | 1997-09-30 | Byk Gulden Lomberg Chem Fab | 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
-
1998
- 1998-03-19 EE EEP199900450A patent/EE03771B1/xx not_active IP Right Cessation
- 1998-03-19 NZ NZ337325A patent/NZ337325A/en unknown
- 1998-03-19 KR KR10-1999-7008744A patent/KR100523422B1/ko not_active IP Right Cessation
- 1998-03-19 SI SI9830668T patent/SI0971922T1/xx unknown
- 1998-03-19 CZ CZ19993397A patent/CZ290548B6/cs not_active IP Right Cessation
- 1998-03-19 PT PT98922622T patent/PT971922E/pt unknown
- 1998-03-19 CU CU1999140A patent/CU23088A3/es not_active IP Right Cessation
- 1998-03-19 EA EA199900777A patent/EA002402B1/ru not_active IP Right Cessation
- 1998-03-19 JP JP54442498A patent/JP4138022B2/ja not_active Expired - Fee Related
- 1998-03-19 AT AT98922622T patent/ATE265455T1/de not_active IP Right Cessation
- 1998-03-19 DK DK98922622T patent/DK0971922T3/da active
- 1998-03-19 ID IDW990927A patent/ID22718A/id unknown
- 1998-03-19 AU AU75208/98A patent/AU740578B2/en not_active Ceased
- 1998-03-19 BR BR9807883-6A patent/BR9807883A/pt not_active IP Right Cessation
- 1998-03-19 CN CNB2003101013227A patent/CN1250546C/zh not_active Expired - Fee Related
- 1998-03-19 ES ES98922622T patent/ES2219890T3/es not_active Expired - Lifetime
- 1998-03-19 IL IL13140798A patent/IL131407A0/xx not_active IP Right Cessation
- 1998-03-19 SK SK1297-99A patent/SK283288B6/sk not_active IP Right Cessation
- 1998-03-19 DE DE69823493T patent/DE69823493T2/de not_active Expired - Fee Related
- 1998-03-19 US US09/381,617 patent/US6197783B1/en not_active Expired - Fee Related
- 1998-03-19 CN CN98803636A patent/CN1251102A/zh active Pending
- 1998-03-19 CA CA002284747A patent/CA2284747A1/en not_active Abandoned
- 1998-03-19 UA UA99105774A patent/UA61102C2/uk unknown
- 1998-03-19 TR TR1999/02257T patent/TR199902257T2/xx unknown
- 1998-03-19 PL PL335699A patent/PL190803B1/pl not_active IP Right Cessation
-
1999
- 1999-03-19 RS YUP-474/99A patent/RS49617B/sr unknown
- 1999-08-23 IS IS5161A patent/IS2077B/is unknown
- 1999-08-30 BG BG103696A patent/BG64157B1/bg unknown
- 1999-09-21 NO NO19994584A patent/NO314084B1/no not_active IP Right Cessation
-
2004
- 2004-12-28 HK HK04110284A patent/HK1067365A1/xx not_active IP Right Cessation
-
2005
- 2005-09-14 CY CY0500050A patent/CY2538B1/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |