NO313009B1 - Forbindelser for inhibering av mavesyresekresjon, farmasöytisk formulering inneholdende slike forbindelser, deresanvendelse og fremgangsmåte for deres fremstilling - Google Patents
Forbindelser for inhibering av mavesyresekresjon, farmasöytisk formulering inneholdende slike forbindelser, deresanvendelse og fremgangsmåte for deres fremstilling Download PDFInfo
- Publication number
- NO313009B1 NO313009B1 NO19994078A NO994078A NO313009B1 NO 313009 B1 NO313009 B1 NO 313009B1 NO 19994078 A NO19994078 A NO 19994078A NO 994078 A NO994078 A NO 994078A NO 313009 B1 NO313009 B1 NO 313009B1
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- Norway
- Prior art keywords
- formula
- compound
- compounds
- compound according
- pyridine
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 186
- 238000002360 preparation method Methods 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 8
- 230000005764 inhibitory process Effects 0.000 title description 6
- 210000002784 stomach Anatomy 0.000 title description 6
- 230000009858 acid secretion Effects 0.000 title description 5
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000012442 inert solvent Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000027119 gastric acid secretion Effects 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 210000001156 gastric mucosa Anatomy 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 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 2
- 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 2
- ZXWOLERJACOHEC-UHFFFAOYSA-N [8-[(2,6-dimethylphenyl)methylamino]-2-methylimidazo[1,2-a]pyridin-3-yl]methanol Chemical compound C=1C=CN2C(CO)=C(C)N=C2C=1NCC1=C(C)C=CC=C1C ZXWOLERJACOHEC-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- OSVXOXPIOPBKQC-UHFFFAOYSA-N n-[(2,6-diethylphenyl)methyl]-2,3,6-trimethylimidazo[1,2-a]pyridin-8-amine Chemical compound CCC1=CC=CC(CC)=C1CNC1=CC(C)=CN2C1=NC(C)=C2C OSVXOXPIOPBKQC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 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 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 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 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 175
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 118
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 60
- 230000015572 biosynthetic process Effects 0.000 description 57
- 238000003786 synthesis reaction Methods 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- 238000005160 1H NMR spectroscopy Methods 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 39
- 238000010992 reflux Methods 0.000 description 37
- 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
- 239000000741 silica gel Substances 0.000 description 36
- 229910002027 silica gel Inorganic materials 0.000 description 36
- 239000002904 solvent Substances 0.000 description 36
- 238000004440 column chromatography Methods 0.000 description 33
- 239000003480 eluent Substances 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 30
- 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 24
- 239000000047 product Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 13
- 239000003208 petroleum Substances 0.000 description 13
- 235000009518 sodium iodide Nutrition 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 230000002496 gastric effect Effects 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 239000012258 stirred mixture Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- -1 heterocyclic carboxylic Chemical class 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- HPVRFWQMBYLJRL-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1CCl HPVRFWQMBYLJRL-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- QOJQBWSZHCKOLL-UHFFFAOYSA-N 2,6-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C)=C1C=O QOJQBWSZHCKOLL-UHFFFAOYSA-N 0.000 description 6
- HYFDMAKFLLWGOK-UHFFFAOYSA-N 2-(bromomethyl)-5-fluoro-1,3-dimethylbenzene Chemical compound CC1=CC(F)=CC(C)=C1CBr HYFDMAKFLLWGOK-UHFFFAOYSA-N 0.000 description 6
- 108091006112 ATPases Proteins 0.000 description 6
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VZOPRCCTKLAGPN-ZFJVMAEJSA-L potassium;sodium;(2r,3r)-2,3-dihydroxybutanedioate;tetrahydrate Chemical compound O.O.O.O.[Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O VZOPRCCTKLAGPN-ZFJVMAEJSA-L 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- UIEARKBMUATCNI-UHFFFAOYSA-N 2-(chloromethyl)-1-ethyl-3-methylbenzene Chemical compound CCC1=CC=CC(C)=C1CCl UIEARKBMUATCNI-UHFFFAOYSA-N 0.000 description 4
- BNBOUFHCTIFWHN-UHFFFAOYSA-N 3-bromobutan-2-one Chemical compound CC(Br)C(C)=O BNBOUFHCTIFWHN-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
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 210000004379 membrane Anatomy 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance 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
- 239000013078 crystal Substances 0.000 description 3
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 210000004051 gastric juice Anatomy 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 208000027866 inflammatory disease Diseases 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 3
- 229940074446 sodium potassium tartrate tetrahydrate Drugs 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SANMLBOHAXBMMS-UHFFFAOYSA-N 1-ethyl-3-fluoro-5-methylbenzene Chemical compound CCC1=CC(C)=CC(F)=C1 SANMLBOHAXBMMS-UHFFFAOYSA-N 0.000 description 2
- IHPYMWDTONKSCO-UHFFFAOYSA-N 2,2'-piperazine-1,4-diylbisethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCN(CCS(O)(=O)=O)CC1 IHPYMWDTONKSCO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- PESVDKISSIUPTJ-UHFFFAOYSA-N 2,6-diethylbenzaldehyde Chemical compound CCC1=CC=CC(CC)=C1C=O PESVDKISSIUPTJ-UHFFFAOYSA-N 0.000 description 2
- FHHVEUQPKNBWMT-UHFFFAOYSA-N 2-(bromomethyl)-1-chloro-3,5-dimethylbenzene Chemical compound CC1=CC(C)=C(CBr)C(Cl)=C1 FHHVEUQPKNBWMT-UHFFFAOYSA-N 0.000 description 2
- TVNROUIUGVLBOP-UHFFFAOYSA-N 2-(bromomethyl)-1-ethyl-5-fluoro-3-methylbenzene Chemical compound CCC1=CC(F)=CC(C)=C1CBr TVNROUIUGVLBOP-UHFFFAOYSA-N 0.000 description 2
- FYIVZEYEURWVDB-UHFFFAOYSA-N 2-(bromomethyl)-5-chloro-1,3-dimethylbenzene Chemical compound CC1=CC(Cl)=CC(C)=C1CBr FYIVZEYEURWVDB-UHFFFAOYSA-N 0.000 description 2
- FANMFAXGQCUEDQ-UHFFFAOYSA-N 3-[(2,6-dimethylphenyl)methoxy]-5-methylpyridin-2-amine Chemical compound CC1=CN=C(N)C(OCC=2C(=CC=CC=2C)C)=C1 FANMFAXGQCUEDQ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
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- ZQUAVILLCXTKTF-UHFFFAOYSA-H bismuth;tripotassium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [K+].[K+].[K+].[Bi+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZQUAVILLCXTKTF-UHFFFAOYSA-H 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
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- 238000004364 calculation method Methods 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
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- 229960000603 cefalotin Drugs 0.000 description 1
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- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
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- UVTLYMPJRXHJGK-UHFFFAOYSA-N ethyl 8-[(2,6-diethylphenyl)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(CC)C=CC=C1CC UVTLYMPJRXHJGK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LBINVIAEGIDNJC-UHFFFAOYSA-N ethyl 8-[(2-ethyl-4-fluoro-6-methylphenyl)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=C(F)C=C1CC LBINVIAEGIDNJC-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 235000019253 formic acid Nutrition 0.000 description 1
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- 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
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- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 229960000318 kanamycin Drugs 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 229930182823 kanamycin A Natural products 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 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 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229960000564 nitrofurantoin Drugs 0.000 description 1
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 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
- 239000008188 pellet Substances 0.000 description 1
- 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 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
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 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
- 150000007660 quinolones Chemical class 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000011084 recovery Methods 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
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 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
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- 238000007738 vacuum evaporation Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000001993 wax Substances 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9700661A SE9700661D0 (sv) | 1997-02-25 | 1997-02-25 | New compounds |
| PCT/SE1998/000275 WO1998037080A1 (en) | 1997-02-25 | 1998-02-17 | Compounds for inhibition of gastric acid secretion |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO994078D0 NO994078D0 (no) | 1999-08-24 |
| NO994078L NO994078L (no) | 1999-08-24 |
| NO313009B1 true NO313009B1 (no) | 2002-07-29 |
Family
ID=20405920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19994078A NO313009B1 (no) | 1997-02-25 | 1999-08-24 | Forbindelser for inhibering av mavesyresekresjon, farmasöytisk formulering inneholdende slike forbindelser, deresanvendelse og fremgangsmåte for deres fremstilling |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US6265415B1 (xx) |
| EP (1) | EP0971920B1 (xx) |
| JP (1) | JP2001512477A (xx) |
| KR (1) | KR20000075622A (xx) |
| CN (1) | CN1100056C (xx) |
| AR (1) | AR011134A1 (xx) |
| AT (1) | ATE218569T1 (xx) |
| AU (1) | AU723389B2 (xx) |
| BR (1) | BR9807457A (xx) |
| CA (1) | CA2280008A1 (xx) |
| CZ (1) | CZ291681B6 (xx) |
| DE (1) | DE69805787T2 (xx) |
| DK (1) | DK0971920T3 (xx) |
| EE (1) | EE04016B1 (xx) |
| ES (1) | ES2178169T3 (xx) |
| HK (1) | HK1024248A1 (xx) |
| HU (1) | HUP0000720A3 (xx) |
| ID (1) | ID22218A (xx) |
| IL (1) | IL131122A0 (xx) |
| IS (1) | IS1901B (xx) |
| MY (1) | MY118822A (xx) |
| NO (1) | NO313009B1 (xx) |
| NZ (1) | NZ336878A (xx) |
| PL (1) | PL190379B1 (xx) |
| PT (1) | PT971920E (xx) |
| RU (1) | RU2193036C2 (xx) |
| SE (1) | SE9700661D0 (xx) |
| SK (1) | SK283903B6 (xx) |
| TR (1) | TR199902060T2 (xx) |
| TW (1) | TW568907B (xx) |
| UA (1) | UA64741C2 (xx) |
| WO (1) | WO1998037080A1 (xx) |
| ZA (1) | ZA981134B (xx) |
Families Citing this family (28)
| 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 |
| JPH10502366A (ja) * | 1994-07-01 | 1998-03-03 | リカン・リミテッド | ヘリコバクター・ピロリ抗原タンパク質調製品およびイムノアッセイ |
| AU1463097A (en) * | 1996-01-04 | 1997-08-01 | 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 |
| JP2005506322A (ja) * | 2001-08-31 | 2005-03-03 | カイロン ソチエタ ア レスポンサビリタ リミタータ | Ｈｅｌｉｃｏｂａｃｔｅｒｐｙｌｏｒｉワクチン接種 |
| 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 |
| US6992080B2 (en) | 2002-09-19 | 2006-01-31 | Schering Corporation | Imidazopyridines as cyclin dependent kinase inhibitors |
| CA2517256C (en) * | 2003-02-26 | 2013-04-30 | Sugen, Inc. | Aminoheteroaryl compounds as protein kinase inhibitors |
| EP1606261B1 (en) | 2003-03-10 | 2009-11-04 | Nycomed GmbH | Novel process for the preparation of roflumilast |
| WO2005026164A1 (en) * | 2003-09-18 | 2005-03-24 | Altana Pharma Ag | Pharmacologically active imidazo[4,5-c]pyridines |
| CN1874772A (zh) | 2003-11-03 | 2006-12-06 | 阿斯利康(瑞典)有限公司 | 治疗隐匿性胃食管反流的咪唑并[1,2－a]吡啶衍生物 |
| KR102152809B1 (ko) * | 2004-07-28 | 2020-09-07 | 다케다 야쿠힌 고교 가부시키가이샤 | 피롤로〔2,3-ｃ〕피리딘 화합물, 그 제조 방법 및 용도 |
| KR100958830B1 (ko) | 2004-09-03 | 2010-05-24 | 주식회사유한양행 | 피롤로[2,3-ｃ]피리딘 유도체 및 그의 제조방법 |
| BRPI0514695A (pt) | 2004-09-03 | 2008-06-17 | Yuhan Corp | derivados de pirrol[3, 2-b]piridina e processos para a preparação destes |
| US8148529B2 (en) | 2004-09-03 | 2012-04-03 | Yuhan Corporation | Pyrrolo[3,2-C] pyridine derivatives and processes for the preparation thereof |
| KR101068355B1 (ko) * | 2005-03-09 | 2011-09-28 | 주식회사유한양행 | 신규의 이미다조[1,2-ａ]피리딘 유도체 및 그의 제조방법 |
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| AR055321A1 (es) * | 2005-03-24 | 2007-08-15 | Glaxo Group Ltd | Compuestos de imidazopiridina uso para a fabricacion de un medicamento para el tratamiento o profilaxis de enfermedades o trastornos en los que se requiere un antagonista de una bomba de acido y composicion farmaceutica que lo comprende |
| PL1959955T3 (pl) | 2005-12-05 | 2011-04-29 | Pfizer Prod Inc | Sposób traktowania nieprawidłowego wzrostu komórek |
| WO2007066185A2 (en) | 2005-12-05 | 2007-06-14 | Pfizer Products Inc. | Polymorphs of a c-met/hgfr inhibitor |
| CN110483499A (zh) * | 2009-11-05 | 2019-11-22 | 圣母大学 | 咪唑并[1,2-a]吡啶类化合物及其合成及使用方法 |
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| TW201439090A (zh) * | 2012-11-30 | 2014-10-16 | Astellas Pharma Inc | 咪唑並吡啶化合物 |
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| 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 |
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