NO331505B1 - (-) Enantiomeren av tenatoprazol, farmasoytisk preparat inneholdende denne samt anvendelse av denne for fremstilling av medisinsk preparat for behandling av sykdom - Google Patents
(-) Enantiomeren av tenatoprazol, farmasoytisk preparat inneholdende denne samt anvendelse av denne for fremstilling av medisinsk preparat for behandling av sykdom Download PDFInfo
- Publication number
- NO331505B1 NO331505B1 NO20052798A NO20052798A NO331505B1 NO 331505 B1 NO331505 B1 NO 331505B1 NO 20052798 A NO20052798 A NO 20052798A NO 20052798 A NO20052798 A NO 20052798A NO 331505 B1 NO331505 B1 NO 331505B1
- Authority
- NO
- Norway
- Prior art keywords
- tenatoprazole
- enantiomer
- treatment
- preparation
- pharmaceutically acceptable
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 13
- ZBFDAUIVDSSISP-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-imidazo[4,5-b]pyridine Chemical compound N=1C2=NC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C ZBFDAUIVDSSISP-UHFFFAOYSA-N 0.000 title abstract description 62
- 229950008375 tenatoprazole Drugs 0.000 title abstract description 60
- 201000010099 disease Diseases 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 4-methoxy-3,5-dimethyl-2-pyridyl Chemical group 0.000 claims abstract description 5
- ZBFDAUIVDSSISP-DEOSSOPVSA-N 5-methoxy-2-[(s)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-imidazo[4,5-b]pyridine Chemical compound C([S@](=O)C=1NC2=CC=C(N=C2N=1)OC)C1=NC=C(C)C(OC)=C1C ZBFDAUIVDSSISP-DEOSSOPVSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 10
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 10
- 230000000740 bleeding effect Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 208000010643 digestive system disease Diseases 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 210000002249 digestive system Anatomy 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 206010030216 Oesophagitis Diseases 0.000 claims description 4
- 208000006881 esophagitis Diseases 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 208000023514 Barrett esophagus Diseases 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 230000009858 acid secretion Effects 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 159000000007 calcium salts Chemical class 0.000 claims description 3
- 238000002651 drug therapy Methods 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 230000002035 prolonged effect Effects 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 229940126409 proton pump inhibitor Drugs 0.000 claims description 2
- 239000000612 proton pump inhibitor Substances 0.000 claims description 2
- 208000032843 Hemorrhage Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000034158 bleeding Diseases 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 12
- 229940079593 drug Drugs 0.000 abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 230000001079 digestive effect Effects 0.000 abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000000034 method Methods 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 230000004060 metabolic process Effects 0.000 description 10
- 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 8
- 108010026925 Cytochrome P-450 CYP2C19 Proteins 0.000 description 8
- 230000002496 gastric effect Effects 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 230000003902 lesion Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000035876 healing Effects 0.000 description 6
- 229960000381 omeprazole Drugs 0.000 description 6
- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 6
- 102100029363 Cytochrome P450 2C19 Human genes 0.000 description 5
- 102000018832 Cytochromes Human genes 0.000 description 5
- 108010052832 Cytochromes Proteins 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
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- 241000282472 Canis lupus familiaris Species 0.000 description 4
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- 230000036732 histological change Effects 0.000 description 4
- 238000010606 normalization Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 108010081668 Cytochrome P-450 CYP3A Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 206010013710 Drug interaction Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 208000007107 Stomach Ulcer Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 201000006549 dyspepsia Diseases 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000036470 plasma concentration Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010019375 Helicobacter infections Diseases 0.000 description 2
- 241000590002 Helicobacter pylori Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001262 anti-secretory effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000003821 enantio-separation Methods 0.000 description 2
- 210000004211 gastric acid Anatomy 0.000 description 2
- 201000000052 gastrinoma Diseases 0.000 description 2
- 229940037467 helicobacter pylori Drugs 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229960003174 lansoprazole Drugs 0.000 description 2
- SIXIIKVOZAGHPV-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=C[CH]C2=N1 SIXIIKVOZAGHPV-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 1
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- FPVRDLVBWBBIPI-UHFFFAOYSA-N 2-methylsulfinyl-4-pyridin-2-yl-1h-benzimidazole Chemical class C=12NC(S(=O)C)=NC2=CC=CC=1C1=CC=CC=N1 FPVRDLVBWBBIPI-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- 208000036764 Adenocarcinoma of the esophagus Diseases 0.000 description 1
- 102100039205 Cytochrome P450 3A4 Human genes 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 206010071602 Genetic polymorphism Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010030137 Oesophageal adenocarcinoma Diseases 0.000 description 1
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000008406 drug-drug interaction Effects 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 208000028653 esophageal adenocarcinoma Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000009115 maintenance therapy Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000711 polarimetry Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000000039 preparative column chromatography Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 229960004157 rabeprazole Drugs 0.000 description 1
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- HWEXKRHYVOGVDA-UHFFFAOYSA-M sodium;3-trimethylsilylpropane-1-sulfonate Chemical compound [Na+].C[Si](C)(C)CCCS([O-])(=O)=O HWEXKRHYVOGVDA-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- IBYSTTGVDIFUAY-UHFFFAOYSA-N vanadium monoxide Chemical compound [V]=O IBYSTTGVDIFUAY-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0215949A FR2848555B1 (fr) | 2002-12-16 | 2002-12-16 | Enantiomere(-)du tenatoprazole et son application en therapeutique |
| PCT/FR2003/003746 WO2004060891A1 (fr) | 2002-12-16 | 2003-12-16 | Enantiomere (-) du tenatoprazole et son application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20052798L NO20052798L (no) | 2005-07-04 |
| NO331505B1 true NO331505B1 (no) | 2012-01-16 |
Family
ID=32338855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20052798A NO331505B1 (no) | 2002-12-16 | 2005-06-09 | (-) Enantiomeren av tenatoprazol, farmasoytisk preparat inneholdende denne samt anvendelse av denne for fremstilling av medisinsk preparat for behandling av sykdom |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7034038B2 (ja) |
| EP (1) | EP1572692A1 (ja) |
| JP (1) | JP5230897B2 (ja) |
| KR (3) | KR20120087886A (ja) |
| CN (1) | CN100345849C (ja) |
| AU (1) | AU2003300627B2 (ja) |
| BR (1) | BR0317328A (ja) |
| CA (1) | CA2509899C (ja) |
| FR (1) | FR2848555B1 (ja) |
| IL (1) | IL168782A (ja) |
| MX (1) | MXPA05006419A (ja) |
| NO (1) | NO331505B1 (ja) |
| NZ (1) | NZ540663A (ja) |
| PL (1) | PL215162B1 (ja) |
| RU (1) | RU2310652C2 (ja) |
| WO (1) | WO2004060891A1 (ja) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2845916B1 (fr) * | 2002-10-21 | 2006-07-07 | Negma Gild | Composition pharmaceutique associant le tenatoprazole et un antagoniste des recepteurs h2 a l'histamine |
| FR2845917B1 (fr) * | 2002-10-21 | 2006-07-07 | Negma Gild | Composition pharmaceutique associant le tenatoprazole et un anti-inflammatoire |
| FR2845915B1 (fr) * | 2002-10-21 | 2006-06-23 | Negma Gild | Utilisation du tenatoprazole pour le traitement du reflux gastro-oesophagien |
| FR2848555B1 (fr) * | 2002-12-16 | 2006-07-28 | Negma Gild | Enantiomere(-)du tenatoprazole et son application en therapeutique |
| KR20050123096A (ko) * | 2003-02-24 | 2005-12-29 | 미쯔비시 웰 파마 가부시키가이샤 | 테나토프라졸의 거울상 이성질체 및 치료를 위한 그 용도 |
| FR2871800B1 (fr) * | 2004-06-17 | 2006-08-25 | Sidem Pharma Sa Sa | Sel de sodium monohydrate du s-tenatoprazole et application en therapeutique |
| FR2876101B1 (fr) * | 2004-10-05 | 2007-03-02 | Sidem Pharma Sa Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| WO2006043280A1 (en) * | 2004-10-19 | 2006-04-27 | Council Of Scientific And Industrial Research | Tenatoprazole salts and process of preparation thereof |
| US20060089376A1 (en) * | 2004-10-27 | 2006-04-27 | Joshi Ramesh A | Tenatoprazole salts and process of preparation thereof |
| CN101497623B (zh) * | 2008-01-30 | 2011-01-12 | 山东轩竹医药科技有限公司 | 含有咪唑并吡啶的化合物 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7804231L (sv) | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| SE8204879D0 (sv) | 1982-08-26 | 1982-08-26 | Haessle Ab | Novel chemical intermediates |
| JPH0643426B2 (ja) | 1986-07-25 | 1994-06-08 | 東京田辺製薬株式会社 | イミダゾ〔４，５−ｂ〕ピリジン誘導体、その製造法及びそれを含有する抗潰瘍剤 |
| SE9301830D0 (sv) | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| SE504459C2 (sv) | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
| US6369087B1 (en) | 1999-08-26 | 2002-04-09 | Robert R. Whittle | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| SE9903831D0 (sv) * | 1999-10-22 | 1999-10-22 | Astra Ab | Formulation of substituted benzimidazoles |
| FR2845916B1 (fr) | 2002-10-21 | 2006-07-07 | Negma Gild | Composition pharmaceutique associant le tenatoprazole et un antagoniste des recepteurs h2 a l'histamine |
| FR2845917B1 (fr) | 2002-10-21 | 2006-07-07 | Negma Gild | Composition pharmaceutique associant le tenatoprazole et un anti-inflammatoire |
| FR2845915B1 (fr) | 2002-10-21 | 2006-06-23 | Negma Gild | Utilisation du tenatoprazole pour le traitement du reflux gastro-oesophagien |
| PT1578742E (pt) * | 2002-12-06 | 2013-01-24 | Nycomed Gmbh | Processo para preparar compostos activos opticamente puros |
| FR2848555B1 (fr) * | 2002-12-16 | 2006-07-28 | Negma Gild | Enantiomere(-)du tenatoprazole et son application en therapeutique |
-
2002
- 2002-12-16 FR FR0215949A patent/FR2848555B1/fr not_active Expired - Fee Related
-
2003
- 2003-12-16 EP EP03814481A patent/EP1572692A1/fr not_active Withdrawn
- 2003-12-16 AU AU2003300627A patent/AU2003300627B2/en not_active Ceased
- 2003-12-16 CN CNB2003801062679A patent/CN100345849C/zh not_active Expired - Fee Related
- 2003-12-16 KR KR1020127004143A patent/KR20120087886A/ko not_active Application Discontinuation
- 2003-12-16 PL PL377738A patent/PL215162B1/pl not_active IP Right Cessation
- 2003-12-16 MX MXPA05006419A patent/MXPA05006419A/es active IP Right Grant
- 2003-12-16 CA CA2509899A patent/CA2509899C/fr not_active Expired - Fee Related
- 2003-12-16 WO PCT/FR2003/003746 patent/WO2004060891A1/fr active Application Filing
- 2003-12-16 KR KR1020057011100A patent/KR20050088184A/ko not_active Application Discontinuation
- 2003-12-16 RU RU2005122465/04A patent/RU2310652C2/ru not_active IP Right Cessation
- 2003-12-16 JP JP2004564280A patent/JP5230897B2/ja not_active Expired - Fee Related
- 2003-12-16 BR BR0317328-3A patent/BR0317328A/pt not_active IP Right Cessation
- 2003-12-16 KR KR1020137034689A patent/KR20140022437A/ko not_active Application Discontinuation
- 2003-12-16 US US10/507,485 patent/US7034038B2/en not_active Expired - Fee Related
- 2003-12-16 NZ NZ540663A patent/NZ540663A/en not_active IP Right Cessation
-
2005
- 2005-05-25 IL IL168782A patent/IL168782A/en not_active IP Right Cessation
- 2005-06-09 NO NO20052798A patent/NO331505B1/no not_active IP Right Cessation
-
2006
- 2006-02-01 US US11/344,212 patent/US7652034B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL215162B1 (pl) | 2013-10-31 |
| WO2004060891A1 (fr) | 2004-07-22 |
| KR20050088184A (ko) | 2005-09-02 |
| US7652034B2 (en) | 2010-01-26 |
| JP5230897B2 (ja) | 2013-07-10 |
| JP2006513230A (ja) | 2006-04-20 |
| US20060194832A1 (en) | 2006-08-31 |
| US20050119298A1 (en) | 2005-06-02 |
| CN1726214A (zh) | 2006-01-25 |
| AU2003300627B2 (en) | 2009-07-23 |
| EP1572692A1 (fr) | 2005-09-14 |
| FR2848555B1 (fr) | 2006-07-28 |
| CA2509899A1 (fr) | 2004-07-22 |
| IL168782A (en) | 2013-05-30 |
| BR0317328A (pt) | 2005-11-08 |
| CA2509899C (fr) | 2012-07-03 |
| KR20140022437A (ko) | 2014-02-24 |
| MXPA05006419A (es) | 2006-03-08 |
| US7034038B2 (en) | 2006-04-25 |
| KR20120087886A (ko) | 2012-08-07 |
| NZ540663A (en) | 2007-12-21 |
| NO20052798L (no) | 2005-07-04 |
| AU2003300627A1 (en) | 2004-07-29 |
| CN100345849C (zh) | 2007-10-31 |
| RU2005122465A (ru) | 2006-01-20 |
| PL377738A1 (pl) | 2006-02-20 |
| RU2310652C2 (ru) | 2007-11-20 |
| FR2848555A1 (fr) | 2004-06-18 |
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