CZ291681B6 - Imidazopyridinový derivát, způsob jeho přípravy a použití a farmaceutický prostředek s jeho obsahem - Google Patents
Imidazopyridinový derivát, způsob jeho přípravy a použití a farmaceutický prostředek s jeho obsahem Download PDFInfo
- Publication number
- CZ291681B6 CZ291681B6 CZ19993014A CZ301499A CZ291681B6 CZ 291681 B6 CZ291681 B6 CZ 291681B6 CZ 19993014 A CZ19993014 A CZ 19993014A CZ 301499 A CZ301499 A CZ 301499A CZ 291681 B6 CZ291681 B6 CZ 291681B6
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- CZ
- Czechia
- Prior art keywords
- formula
- compound
- pyridine
- derivative according
- imidazopyridine derivative
- Prior art date
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- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title claims abstract 5
- 238000002360 preparation method Methods 0.000 title claims description 79
- 238000000034 method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims abstract description 6
- 238000011321 prophylaxis Methods 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 115
- 150000005232 imidazopyridines Chemical class 0.000 claims description 39
- 239000004480 active ingredient Substances 0.000 claims description 17
- 239000012442 inert solvent Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- -1 2,6-dimethylbenzylamino-3-hydroxymethyl-2-methylimidazo [1,2-a] pyridine Chemical compound 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 230000027119 gastric acid secretion Effects 0.000 claims description 6
- 210000001156 gastric mucosa Anatomy 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 241000590002 Helicobacter pylori Species 0.000 claims description 3
- PTNPMDOWMLEHSJ-UHFFFAOYSA-N [8-[(2,6-dimethylphenyl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C=1C(C)=CN2C(CO)=C(C)N=C2C=1OCC1=C(C)C=CC=C1C PTNPMDOWMLEHSJ-UHFFFAOYSA-N 0.000 claims description 3
- MMHLWQWTEMTZKC-UHFFFAOYSA-N [8-[(2,6-dimethylphenyl)methylamino]-2,6-dimethylimidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C=1C(C)=CN2C(CO)=C(C)N=C2C=1NCC1=C(C)C=CC=C1C MMHLWQWTEMTZKC-UHFFFAOYSA-N 0.000 claims description 3
- VPWZRONYARJIRI-UHFFFAOYSA-N [8-[(2-ethyl-6-methylphenyl)methylamino]-2,6-dimethylimidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C)=CN2C1=NC(C)=C2CO VPWZRONYARJIRI-UHFFFAOYSA-N 0.000 claims description 3
- XXYWPYVBYQVLKY-UHFFFAOYSA-N [8-[(4-fluoro-2,6-dimethylphenyl)methoxy]-2-methylimidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C=1C=CN2C(CO)=C(C)N=C2C=1OCC1=C(C)C=C(F)C=C1C XXYWPYVBYQVLKY-UHFFFAOYSA-N 0.000 claims description 3
- ZHWSJGHFRJVNLP-UHFFFAOYSA-N [8-[(4-fluoro-2,6-dimethylphenyl)methylamino]-2,6-dimethylimidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C=1C(C)=CN2C(CO)=C(C)N=C2C=1NCC1=C(C)C=C(F)C=C1C ZHWSJGHFRJVNLP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004599 antimicrobial Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229940037467 helicobacter pylori Drugs 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- RPMMKZINBGZQDN-UHFFFAOYSA-N n-[(2-ethyl-4-fluoro-6-methylphenyl)methyl]-2,3,6-trimethylimidazo[1,2-a]pyridin-8-amine Chemical compound CCC1=CC(F)=CC(C)=C1CNC1=CC(C)=CN2C1=NC(C)=C2C RPMMKZINBGZQDN-UHFFFAOYSA-N 0.000 claims description 3
- LUPBLBIGCPPRON-UHFFFAOYSA-N n-[(4-fluoro-2,6-dimethylphenyl)methyl]-2,3-dimethylimidazo[1,2-a]pyridin-8-amine Chemical compound C=1C=CN2C(C)=C(C)N=C2C=1NCC1=C(C)C=C(F)C=C1C LUPBLBIGCPPRON-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- IGORZTUCIDSFDL-UHFFFAOYSA-N [8-[(2,6-diethylphenyl)methylamino]-2,6-dimethylimidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CCC1=CC=CC(CC)=C1CNC1=CC(C)=CN2C1=NC(C)=C2CO IGORZTUCIDSFDL-UHFFFAOYSA-N 0.000 claims description 2
- IVVSNSJMFLZNDJ-UHFFFAOYSA-N [8-[(2-ethyl-4-fluoro-6-methylphenyl)methylamino]-2,6-dimethylimidazo[1,2-a]pyridin-3-yl]methanol Chemical compound CCC1=CC(F)=CC(C)=C1CNC1=CC(C)=CN2C1=NC(C)=C2CO IVVSNSJMFLZNDJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- ZXJBLBADKNTHPO-UHFFFAOYSA-N n-[(2,6-dimethylphenyl)methyl]-2,3,6-trimethylimidazo[1,2-a]pyridin-8-amine Chemical compound C=1C(C)=CN2C(C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1C ZXJBLBADKNTHPO-UHFFFAOYSA-N 0.000 claims description 2
- MFPPVPQUXFXTIV-UHFFFAOYSA-N n-[(2-ethyl-6-methylphenyl)methyl]-2,3,6-trimethylimidazo[1,2-a]pyridin-8-amine Chemical compound CCC1=CC=CC(C)=C1CNC1=CC(C)=CN2C1=NC(C)=C2C MFPPVPQUXFXTIV-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- WYFUNEBAGKOUTL-UHFFFAOYSA-N N-[(4-chloro-2,6-dimethylphenyl)methyl]imidazo[1,2-a]pyridin-2-amine Chemical compound CC1=CC(=CC(=C1CNC2=CN3C=CC=CC3=N2)C)Cl WYFUNEBAGKOUTL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- AXXKYAJAPLKEEE-UHFFFAOYSA-N n-[(4-fluoro-2,6-dimethylphenyl)methyl]-2,3,6-trimethylimidazo[1,2-a]pyridin-8-amine Chemical compound C=1C(C)=CN2C(C)=C(C)N=C2C=1NCC1=C(C)C=C(F)C=C1C AXXKYAJAPLKEEE-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 18
- 230000028327 secretion Effects 0.000 abstract description 5
- 210000002784 stomach Anatomy 0.000 abstract description 5
- 229910052740 iodine Inorganic materials 0.000 abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 215
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- 239000000203 mixture Substances 0.000 description 62
- 238000005160 1H NMR spectroscopy Methods 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 34
- 239000012044 organic layer Substances 0.000 description 32
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 27
- 238000010898 silica gel chromatography Methods 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 25
- 235000011152 sodium sulphate Nutrition 0.000 description 25
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 24
- 239000000047 product Substances 0.000 description 22
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 14
- 235000009518 sodium iodide Nutrition 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 239000011592 zinc chloride Substances 0.000 description 12
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- HYFDMAKFLLWGOK-UHFFFAOYSA-N 2-(bromomethyl)-5-fluoro-1,3-dimethylbenzene Chemical compound CC1=CC(F)=CC(C)=C1CBr HYFDMAKFLLWGOK-UHFFFAOYSA-N 0.000 description 8
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- 238000001704 evaporation Methods 0.000 description 8
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- 238000003756 stirring Methods 0.000 description 7
- ZFKUUYLAFYWZSS-UHFFFAOYSA-N 2,3,6-trimethylimidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC(C)=CN2C(C)=C(C)N=C21 ZFKUUYLAFYWZSS-UHFFFAOYSA-N 0.000 description 6
- HPVRFWQMBYLJRL-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1CCl HPVRFWQMBYLJRL-UHFFFAOYSA-N 0.000 description 6
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- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- RTUABNJRTRJMMS-UHFFFAOYSA-N 2,3-dimethylimidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CN2C(C)=C(C)N=C21 RTUABNJRTRJMMS-UHFFFAOYSA-N 0.000 description 5
- BNBOUFHCTIFWHN-UHFFFAOYSA-N 3-bromobutan-2-one Chemical compound CC(Br)C(C)=O BNBOUFHCTIFWHN-UHFFFAOYSA-N 0.000 description 5
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- JCYLOXBHTIKQGL-UHFFFAOYSA-N ethyl 8-amino-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Chemical compound NC1=CC(C)=CN2C(C(=O)OCC)=C(C)N=C21 JCYLOXBHTIKQGL-UHFFFAOYSA-N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
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- UIEARKBMUATCNI-UHFFFAOYSA-N 2-(chloromethyl)-1-ethyl-3-methylbenzene Chemical compound CCC1=CC=CC(C)=C1CCl UIEARKBMUATCNI-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 3
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- LFWGLUUYTBFHPH-UHFFFAOYSA-N ethyl 8-[(2,6-dimethylphenyl)methylamino]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Chemical compound C=1C(C)=CN2C(C(=O)OCC)=C(C)N=C2C=1NCC1=C(C)C=CC=C1C LFWGLUUYTBFHPH-UHFFFAOYSA-N 0.000 description 3
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- 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 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 108700029318 rat female Proteins 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229940072172 tetracycline antibiotic Drugs 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9700661A SE9700661D0 (sv) | 1997-02-25 | 1997-02-25 | New compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ301499A3 CZ301499A3 (cs) | 2000-02-16 |
| CZ291681B6 true CZ291681B6 (cs) | 2003-04-16 |
Family
ID=20405920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19993014A CZ291681B6 (cs) | 1997-02-25 | 1998-02-17 | Imidazopyridinový derivát, způsob jeho přípravy a použití a farmaceutický prostředek s jeho obsahem |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6265415B1 (enExample) |
| EP (1) | EP0971920B1 (enExample) |
| JP (1) | JP2001512477A (enExample) |
| KR (1) | KR20000075622A (enExample) |
| CN (1) | CN1100056C (enExample) |
| AR (1) | AR011134A1 (enExample) |
| AT (1) | ATE218569T1 (enExample) |
| AU (1) | AU723389B2 (enExample) |
| BR (1) | BR9807457A (enExample) |
| CA (1) | CA2280008A1 (enExample) |
| CZ (1) | CZ291681B6 (enExample) |
| DE (1) | DE69805787T2 (enExample) |
| DK (1) | DK0971920T3 (enExample) |
| EE (1) | EE04016B1 (enExample) |
| ES (1) | ES2178169T3 (enExample) |
| HU (1) | HUP0000720A3 (enExample) |
| ID (1) | ID22218A (enExample) |
| IL (1) | IL131122A0 (enExample) |
| IS (1) | IS1901B (enExample) |
| MY (1) | MY118822A (enExample) |
| NO (1) | NO313009B1 (enExample) |
| NZ (1) | NZ336878A (enExample) |
| PL (1) | PL190379B1 (enExample) |
| PT (1) | PT971920E (enExample) |
| RU (1) | RU2193036C2 (enExample) |
| SE (1) | SE9700661D0 (enExample) |
| SK (1) | SK283903B6 (enExample) |
| TR (1) | TR199902060T2 (enExample) |
| TW (1) | TW568907B (enExample) |
| UA (1) | UA64741C2 (enExample) |
| WO (1) | WO1998037080A1 (enExample) |
| ZA (1) | ZA981134B (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7141244B1 (en) * | 1992-03-02 | 2006-11-28 | Chiron Srl | Helicobacter pylori proteins useful for vaccines and diagnostics |
| JPH10502365A (ja) * | 1994-07-01 | 1998-03-03 | リカン・リミテッド | ヘリコバクタータンパク質およびワクチン |
| GB2324093A (en) * | 1996-01-04 | 1998-10-14 | Rican Limited | Helicobacter pylori bacterioferritin |
| SE9602286D0 (sv) | 1996-06-10 | 1996-06-10 | Astra Ab | New compounds |
| SE9704404D0 (sv) | 1997-11-28 | 1997-11-28 | Astra Ab | New compounds |
| SE9802794D0 (sv) * | 1998-08-21 | 1998-08-21 | Astra Ab | New compounds |
| DE10001037C1 (de) * | 2000-01-13 | 2001-12-13 | Byk Gulden Lomberg Chem Fab | Verfahren und Zwischenprodukte zur Herstellung von Imidazopyridinen |
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| EP1423142A1 (en) * | 2001-08-31 | 2004-06-02 | Chiron SRL. | Helicobacter pylori vaccination with a combination of caga, vaca and nap proteins |
| DE10145457A1 (de) | 2001-09-14 | 2003-04-03 | Basf Ag | Substituierte Imidazo[1,2-a]-5,6,7,8-tetrahydropyridin-8-one, Verfahren zu ihrer Herstellung, sowie deren Verwendung zur Herstellung von Imidazo[1,2,-a]pyridinen |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| CA2499639C (en) | 2002-09-19 | 2011-11-08 | Schering Corporation | Imidazopyridines as cyclin dependent kinase inhibitors |
| DK1603570T5 (da) * | 2003-02-26 | 2013-12-09 | Sugen Inc | Aminoheteroarylforbindelser som proteinkinaseinhibitorer |
| ES2335498T3 (es) | 2003-03-10 | 2010-03-29 | Nycomed Gmbh | Nuevo proceso para la preparacion de reflumilast. |
| SE0301904D0 (sv) * | 2003-06-26 | 2003-06-26 | Astrazeneca Ab | Novel imidazopyridine compound II with therapeutic effect |
| WO2005026164A1 (en) * | 2003-09-18 | 2005-03-24 | Altana Pharma Ag | Pharmacologically active imidazo[4,5-c]pyridines |
| CA2544325A1 (en) | 2003-11-03 | 2005-05-12 | Astrazeneca Ab | Imidazo [1,2-a] pyridine derivatives for the treatment of silent gastro-esophageal reflux |
| SE0303451D0 (sv) * | 2003-12-18 | 2003-12-18 | Astrazeneca Ab | New compounds |
| TW200606163A (en) * | 2004-04-22 | 2006-02-16 | Eisai Co Ltd | Imidazopyridine compound |
| ATE527258T1 (de) * | 2004-07-28 | 2011-10-15 | Takeda Pharmaceutical | Pyrroloä2,3-cüpyridinverbindung, verfahren zu deren herstellung und anwendung |
| KR100958829B1 (ko) | 2004-09-03 | 2010-05-25 | 주식회사유한양행 | 피롤로[2,3-ｃ]피리딘 유도체 및 그의 제조방법 |
| EP1784402B1 (en) | 2004-09-03 | 2011-08-03 | Yuhan Corporation | PYRROLO[3,2-c]PYRIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF |
| MX2007002219A (es) * | 2004-09-03 | 2007-05-04 | Yuhan Corp | Derivados de pirrolo [3,2-b ] piridina y procesos para su preparacion. |
| KR101068355B1 (ko) * | 2005-03-09 | 2011-09-28 | 주식회사유한양행 | 신규의 이미다조[1,2-ａ]피리딘 유도체 및 그의 제조방법 |
| EP2258350B1 (en) * | 2005-03-16 | 2014-12-24 | Takeda GmbH | Taste masked dosage form containing roflumilast |
| WO2006100119A1 (en) * | 2005-03-24 | 2006-09-28 | Glaxo Group Limited | Derivatives of imidazo (1,2-a) pyridine useful as medicaments for treating gastrointestinal diseases |
| US7825137B2 (en) | 2005-12-05 | 2010-11-02 | Pfizer Inc. | Method of treating abnormal cell growth |
| DK1963302T3 (da) | 2005-12-05 | 2013-04-02 | Pfizer Prod Inc | Polymorfer af en C-MET/HGFR-inhibitor |
| FR2903107B1 (fr) * | 2006-07-03 | 2008-08-22 | Sanofi Aventis Sa | Derives d'imidazopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
| EP2496578A4 (en) * | 2009-11-05 | 2013-08-21 | Univ Notre Dame Du Lac | IMIDAZO [1,2-A] PYRIDINE COMPOUNDS, THEIR SYNTHESIS AND METHODS OF USE THEREOF |
| EA201391769A1 (ru) | 2011-05-30 | 2014-04-30 | Астеллас Фарма Инк. | Имидазопиридиновые соединения |
| JP6056872B2 (ja) * | 2012-11-30 | 2017-01-11 | アステラス製薬株式会社 | イミダゾピリジン化合物 |
| CN120117960A (zh) * | 2025-05-12 | 2025-06-10 | 天津全和诚科技有限责任公司 | 一种杂质化合物及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA81219B (en) * | 1980-01-23 | 1982-01-27 | Schering Corp | Imidazo (1,2-a) pyridines ,process for their preparation and pharmaceutical compositions containing them |
| US4725601A (en) | 1985-06-04 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers |
| EP0228006A1 (en) * | 1985-12-16 | 1987-07-08 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
| HU201551B (en) * | 1988-02-03 | 1990-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 4-oxo-4h-pyrido(1,2-a)pyrimidine-3-carboxylic acid amide derivatives and pharmaceutical compositions comprising same |
-
1997
- 1997-02-25 SE SE9700661A patent/SE9700661D0/xx unknown
-
1998
- 1998-02-11 ZA ZA981134A patent/ZA981134B/xx unknown
- 1998-02-11 AR ARP980100614A patent/AR011134A1/es active IP Right Grant
- 1998-02-17 PL PL98335485A patent/PL190379B1/pl not_active IP Right Cessation
- 1998-02-17 EE EEP199900367A patent/EE04016B1/xx not_active IP Right Cessation
- 1998-02-17 CZ CZ19993014A patent/CZ291681B6/cs not_active IP Right Cessation
- 1998-02-17 SK SK1099-99A patent/SK283903B6/sk unknown
- 1998-02-17 AT AT98907306T patent/ATE218569T1/de not_active IP Right Cessation
- 1998-02-17 NZ NZ336878A patent/NZ336878A/en unknown
- 1998-02-17 CA CA002280008A patent/CA2280008A1/en not_active Abandoned
- 1998-02-17 HU HU0000720A patent/HUP0000720A3/hu unknown
- 1998-02-17 TW TW087102208A patent/TW568907B/zh active
- 1998-02-17 EP EP98907306A patent/EP0971920B1/en not_active Expired - Lifetime
- 1998-02-17 AU AU63147/98A patent/AU723389B2/en not_active Ceased
- 1998-02-17 BR BR9807457-1A patent/BR9807457A/pt not_active IP Right Cessation
- 1998-02-17 PT PT98907306T patent/PT971920E/pt unknown
- 1998-02-17 ES ES98907306T patent/ES2178169T3/es not_active Expired - Lifetime
- 1998-02-17 IL IL13112298A patent/IL131122A0/xx not_active IP Right Cessation
- 1998-02-17 DE DE69805787T patent/DE69805787T2/de not_active Expired - Fee Related
- 1998-02-17 KR KR1019997007685A patent/KR20000075622A/ko not_active Abandoned
- 1998-02-17 TR TR1999/02060T patent/TR199902060T2/xx unknown
- 1998-02-17 UA UA99084654A patent/UA64741C2/uk unknown
- 1998-02-17 ID IDW990903A patent/ID22218A/id unknown
- 1998-02-17 WO PCT/SE1998/000275 patent/WO1998037080A1/en not_active Ceased
- 1998-02-17 RU RU99120178/04A patent/RU2193036C2/ru not_active IP Right Cessation
- 1998-02-17 JP JP53654998A patent/JP2001512477A/ja not_active Ceased
- 1998-02-17 US US09/043,040 patent/US6265415B1/en not_active Expired - Lifetime
- 1998-02-17 CN CN98802784A patent/CN1100056C/zh not_active Expired - Fee Related
- 1998-02-17 DK DK98907306T patent/DK0971920T3/da active
- 1998-02-23 MY MYPI98000774A patent/MY118822A/en unknown
-
1999
- 1999-08-05 IS IS5148A patent/IS1901B/is unknown
- 1999-08-24 NO NO19994078A patent/NO313009B1/no unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20060217 |