NO884231L - Fremgangsmaate for fremstilling av terapeutisk aktive imidazopyridin-derivater. - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive imidazopyridin-derivater.Info
- Publication number
- NO884231L NO884231L NO88884231A NO884231A NO884231L NO 884231 L NO884231 L NO 884231L NO 88884231 A NO88884231 A NO 88884231A NO 884231 A NO884231 A NO 884231A NO 884231 L NO884231 L NO 884231L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- methyl
- amino
- salt
- propynyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 37
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000005232 imidazopyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 150000003839 salts Chemical class 0.000 claims abstract description 64
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- -1 imidazopyridine compound Chemical class 0.000 claims description 147
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 9
- RPRUCFCRMFWFGW-UHFFFAOYSA-N methyl n-[3-methyl-2-[[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC=CN2C1=NC(C)=C2CC#C RPRUCFCRMFWFGW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000006722 reduction reaction Methods 0.000 claims description 5
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 208000025865 Ulcer Diseases 0.000 abstract description 4
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 4
- 231100000397 ulcer Toxicity 0.000 abstract description 4
- 230000000767 anti-ulcer Effects 0.000 abstract description 3
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 238000004519 manufacturing process Methods 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 125000001589 carboacyl group Chemical group 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- BDQNBWFURXUSAJ-UHFFFAOYSA-N methyl n-[2-(chloromethyl)-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CCl BDQNBWFURXUSAJ-UHFFFAOYSA-N 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- WYGLCSFHIBLIKZ-UHFFFAOYSA-N 2-oxohex-5-yn-3-yl methanesulfonate Chemical compound C#CCC(C(=O)C)OS(C)(=O)=O WYGLCSFHIBLIKZ-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- XPOWYMZSOYKPTP-UHFFFAOYSA-N n-[(2-amino-6-methylphenyl)methyl]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-amine Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1N XPOWYMZSOYKPTP-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- TYSKGOAZKBLRRG-UHFFFAOYSA-N 2-hydroxy-n-[3-methyl-2-[[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]phenyl]propanamide Chemical compound CC(O)C(=O)NC1=CC=CC(C)=C1CNC1=CC=CN2C1=NC(C)=C2CC#C TYSKGOAZKBLRRG-UHFFFAOYSA-N 0.000 description 4
- QYDGXNMMRPTHHZ-UHFFFAOYSA-N 2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CN2C(CC#C)=C(C)N=C21 QYDGXNMMRPTHHZ-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- BRAYBQOXUOLFNO-UHFFFAOYSA-N tert-butyl n-[3-methyl-2-[[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]phenyl]carbamate Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1NC(=O)OC(C)(C)C BRAYBQOXUOLFNO-UHFFFAOYSA-N 0.000 description 4
- LOIHCAGCQVZRTR-UHFFFAOYSA-N (2-amino-6-methylphenyl)methanol Chemical compound CC1=CC=CC(N)=C1CO LOIHCAGCQVZRTR-UHFFFAOYSA-N 0.000 description 3
- SHPUGBIHKJHKFK-UHFFFAOYSA-N 2-hydroxy-n-[3-methyl-2-[[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]phenyl]acetamide Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1NC(=O)CO SHPUGBIHKJHKFK-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZGGCWWJBDJEBKZ-UHFFFAOYSA-N [1-[3-methyl-2-[[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]anilino]-1-oxopropan-2-yl] acetate Chemical compound CC(=O)OC(C)C(=O)NC1=CC=CC(C)=C1CNC1=CC=CN2C1=NC(C)=C2CC#C ZGGCWWJBDJEBKZ-UHFFFAOYSA-N 0.000 description 3
- QAKHLHYJCWDMDX-UHFFFAOYSA-N [2-[3-methyl-2-[[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]anilino]-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)NC1=CC=CC(C)=C1CNC1=CC=CN2C1=NC(C)=C2CC#C QAKHLHYJCWDMDX-UHFFFAOYSA-N 0.000 description 3
- KLDRRRNSUUGDQL-UHFFFAOYSA-N [3-methyl-2-[[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]phenyl]urea Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1NC(N)=O KLDRRRNSUUGDQL-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 230000009858 acid secretion Effects 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- IJOYUOANBXRQRC-UHFFFAOYSA-N methyl 8-[[2-(methoxycarbonylamino)-6-methylphenyl]methylamino]-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC(C(=O)OC)=CN2C1=NC(C)=C2CC#C IJOYUOANBXRQRC-UHFFFAOYSA-N 0.000 description 3
- FODYBFAMPQBNIP-UHFFFAOYSA-N methyl n-[2-[[(2,5-dimethyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC=C(C)N2C1=NC(C)=C2CC#C FODYBFAMPQBNIP-UHFFFAOYSA-N 0.000 description 3
- SYIAYIILRXUVFX-UHFFFAOYSA-N methyl n-[2-[[(2-aminopyridin-3-yl)amino]methyl]-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC=CN=C1N SYIAYIILRXUVFX-UHFFFAOYSA-N 0.000 description 3
- XINSFTKRKITMMP-UHFFFAOYSA-N methyl n-[2-[[(5-acetamido-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC=C(NC(C)=O)N2C1=NC(C)=C2CC#C XINSFTKRKITMMP-UHFFFAOYSA-N 0.000 description 3
- JBAOTOGOHWOACG-UHFFFAOYSA-N methyl n-[2-[[(6-acetamido-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC(NC(C)=O)=CN2C1=NC(C)=C2CC#C JBAOTOGOHWOACG-UHFFFAOYSA-N 0.000 description 3
- OMTXYGOYSSMFLX-UHFFFAOYSA-N methyl n-[2-[[(6-chloro-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC(Cl)=CN2C1=NC(C)=C2CC#C OMTXYGOYSSMFLX-UHFFFAOYSA-N 0.000 description 3
- VIUQPQCGNYVUTH-UHFFFAOYSA-N methyl n-[2-[[[6-(dimethylsulfamoyl)-2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl]amino]methyl]-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC(S(=O)(=O)N(C)C)=CN2C1=NC(C)=C2CC#C VIUQPQCGNYVUTH-UHFFFAOYSA-N 0.000 description 3
- NYZSHRYPSPJIRM-UHFFFAOYSA-N methyl n-[3-methyl-2-[[(2-methyl-6-nitro-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC([N+]([O-])=O)=CN2C1=NC(C)=C2CC#C NYZSHRYPSPJIRM-UHFFFAOYSA-N 0.000 description 3
- BXAAGXQBOOAKDI-UHFFFAOYSA-N methyl n-[3-methyl-2-[[[2-methyl-3-prop-2-ynyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-8-yl]amino]methyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC(C(F)(F)F)=CN2C1=NC(C)=C2CC#C BXAAGXQBOOAKDI-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- DRMCULNGNIWVKD-UHFFFAOYSA-N n-[[3-methyl-2-[[(2-methyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]phenyl]carbamothioyl]benzamide Chemical compound C=1C=CN2C(CC#C)=C(C)N=C2C=1NCC1=C(C)C=CC=C1NC(=S)NC(=O)C1=CC=CC=C1 DRMCULNGNIWVKD-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
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- WWZFGZJNWIFEQE-UHFFFAOYSA-N methyl n-[2-[[(2,6-dimethyl-3-prop-2-ynylimidazo[1,2-a]pyridin-8-yl)amino]methyl]-3-methylphenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C)=C1CNC1=CC(C)=CN2C1=NC(C)=C2CC#C WWZFGZJNWIFEQE-UHFFFAOYSA-N 0.000 description 1
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- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878722488A GB8722488D0 (en) | 1987-09-24 | 1987-09-24 | Imidazopyridine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO884231D0 NO884231D0 (no) | 1988-09-23 |
| NO884231L true NO884231L (no) | 1989-03-28 |
Family
ID=10624306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO88884231A NO884231L (no) | 1987-09-24 | 1988-09-23 | Fremgangsmaate for fremstilling av terapeutisk aktive imidazopyridin-derivater. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4920129A (de) |
| EP (1) | EP0308917A3 (de) |
| JP (1) | JPH01151579A (de) |
| KR (1) | KR890005100A (de) |
| CN (1) | CN1033628A (de) |
| AU (1) | AU2278388A (de) |
| DK (1) | DK532088A (de) |
| FI (1) | FI884318A (de) |
| GB (1) | GB8722488D0 (de) |
| HU (1) | HU201934B (de) |
| IL (1) | IL87809A0 (de) |
| NO (1) | NO884231L (de) |
| ZA (1) | ZA886831B (de) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112834A (en) * | 1987-07-16 | 1992-05-12 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Imidazole protectorant for the stomach and intestine |
| EP0532754A4 (en) * | 1990-05-25 | 1994-08-24 | Yamanouchi Pharma Co Ltd | Tetrahydroimidazopyridine derivative or its salt |
| EP0471236B1 (de) * | 1990-07-30 | 1995-03-15 | Takeda Chemical Industries, Ltd. | Imidazopyridinderivate und ihre Verwendung |
| IL108520A (en) * | 1993-02-15 | 1997-09-30 | Byk Gulden Lomberg Chem Fab | 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| UA48122C2 (uk) * | 1993-10-11 | 2002-08-15 | Бік Гульден Ломберг Хеміше Фабрік Гмбх | АЛКОКСІАЛКІЛКАРБАМАТИ ІМІДАЗО[1,2-а]ПІРИДИНІВ, СПОСІБ ЇХ ОДЕРЖАННЯ ТА ЛІКАРСЬКИЙ ЗАСІБ НА ЇХ ОСНОВІ |
| EP0773945A1 (de) * | 1994-07-28 | 1997-05-21 | Byk Gulden Lomberg Chemische Fabrik GmbH | Acylimidazopyridine |
| WO1996003403A1 (de) * | 1994-07-28 | 1996-02-08 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzylimidazopyridine |
| SK197A3 (en) * | 1994-07-28 | 1997-06-04 | Byk Gulden Lomberg Chem Fab | Imidazopyridine-azolidinones, preparation method thereof, pharmaceutical composition containing same and their use |
| WO1996003402A1 (de) * | 1994-07-28 | 1996-02-08 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Halogenimidazopyridine |
| WO1997027193A1 (de) * | 1996-01-26 | 1997-07-31 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Halogenimidazopyridine |
| DE59712297D1 (de) * | 1996-01-26 | 2005-06-09 | Altana Pharma Ag | 3-alkylimidazopyridine |
| SE9801526D0 (sv) * | 1998-04-29 | 1998-04-29 | Astra Ab | New compounds |
| US20050037490A1 (en) * | 1999-10-29 | 2005-02-17 | Lawrence Rosenberg | Medium for preparing dedifferentiated cells |
| US6900324B2 (en) | 2000-09-07 | 2005-05-31 | Astrazeneca Ab | Process for preparing a substituted imidazopyridine compound |
| SE0003186D0 (sv) * | 2000-09-07 | 2000-09-07 | Astrazeneca Ab | New process |
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| 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 |
| CA2503290C (en) | 2003-03-10 | 2012-12-04 | Altana Pharma Ag | Novel process for the preparation of roflumilast |
| 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 |
| EP1709155B1 (de) * | 2003-12-31 | 2013-10-02 | Chesterford Enterprises Limited | Verbindungen und Zusammensetzungen zur Behandlung dysproliferativer Erkrankungen und Methoden zu deren Verwendung |
| US20080287399A1 (en) * | 2004-12-14 | 2008-11-20 | Astrazeneca Ab | Substituted Aminopyridines and Uses Thereof |
| CA2601250C (en) * | 2005-03-16 | 2014-10-28 | Nycomed Gmbh | Taste masked dosage form containing roflumilast |
| KR102278760B1 (ko) * | 2012-12-20 | 2021-07-20 | 큉-빈 루 | 방사선과 조합하여 사용하는 할로겐- 및 디아미노-를 포함하는 방사선 증감제 화합물 |
| US9623047B2 (en) | 2012-12-27 | 2017-04-18 | Photo Finish Supplements, Llc | Composition and method for improving gastrointestinal health of equine |
| KR101777971B1 (ko) | 2016-07-05 | 2017-09-12 | 제일약품주식회사 | 이미다조[1,2-a]피리딘 유도체, 이의 제조방법 및 이의 용도 |
| US12036286B2 (en) | 2021-03-18 | 2024-07-16 | Seagen Inc. | Selective drug release from internalized conjugates of biologically active compounds |
Family Cites Families (3)
| 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 |
| US4831041A (en) * | 1986-11-26 | 1989-05-16 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
-
1987
- 1987-09-24 GB GB878722488A patent/GB8722488D0/en active Pending
-
1988
- 1988-09-13 ZA ZA886831A patent/ZA886831B/xx unknown
- 1988-09-19 IL IL87809A patent/IL87809A0/xx unknown
- 1988-09-21 FI FI884318A patent/FI884318A/fi not_active Application Discontinuation
- 1988-09-22 US US07/247,657 patent/US4920129A/en not_active Expired - Fee Related
- 1988-09-22 JP JP63238522A patent/JPH01151579A/ja active Pending
- 1988-09-22 EP EP88115541A patent/EP0308917A3/de not_active Withdrawn
- 1988-09-23 CN CN88106859A patent/CN1033628A/zh active Pending
- 1988-09-23 DK DK532088A patent/DK532088A/da not_active Application Discontinuation
- 1988-09-23 HU HU884996A patent/HU201934B/hu not_active IP Right Cessation
- 1988-09-23 KR KR1019880012440A patent/KR890005100A/ko not_active Application Discontinuation
- 1988-09-23 NO NO88884231A patent/NO884231L/no unknown
- 1988-09-23 AU AU22783/88A patent/AU2278388A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| GB8722488D0 (en) | 1987-10-28 |
| US4920129A (en) | 1990-04-24 |
| EP0308917A2 (de) | 1989-03-29 |
| JPH01151579A (ja) | 1989-06-14 |
| DK532088D0 (da) | 1988-09-23 |
| HUT48245A (en) | 1989-05-29 |
| CN1033628A (zh) | 1989-07-05 |
| NO884231D0 (no) | 1988-09-23 |
| ZA886831B (en) | 1989-05-30 |
| EP0308917A3 (de) | 1990-07-11 |
| FI884318A (fi) | 1989-03-25 |
| FI884318A0 (fi) | 1988-09-21 |
| HU201934B (en) | 1991-01-28 |
| KR890005100A (ko) | 1989-05-11 |
| AU2278388A (en) | 1989-04-06 |
| DK532088A (da) | 1989-03-25 |
| IL87809A0 (en) | 1989-03-31 |
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