JPH11501049A - イミダゾ〔１，２−ａ〕ピリジン誘導体 - Google Patents
イミダゾ〔１，２−ａ〕ピリジン誘導体Info
- Publication number
- JPH11501049A JPH11501049A JP8529971A JP52997196A JPH11501049A JP H11501049 A JPH11501049 A JP H11501049A JP 8529971 A JP8529971 A JP 8529971A JP 52997196 A JP52997196 A JP 52997196A JP H11501049 A JPH11501049 A JP H11501049A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- alkyl
- phenyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 182
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims abstract description 17
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 32
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 32
- 229910052794 bromium Inorganic materials 0.000 claims description 32
- -1 R1And RTwoIs H Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 11
- 230000001404 mediated effect Effects 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- KVVJDDVNYVCFDS-UHFFFAOYSA-N 1-[3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridin-8-yl]ethanone Chemical compound N1=C2C(C(=O)C)=CC=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 KVVJDDVNYVCFDS-UHFFFAOYSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 241000282412 Homo Species 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 229940124639 Selective inhibitor Drugs 0.000 abstract description 4
- 208000002193 Pain Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 206010061218 Inflammation Diseases 0.000 abstract description 2
- 206010037660 Pyrexia Diseases 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000377 silicon dioxide Substances 0.000 description 18
- 238000001514 detection method Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 7
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000008101 lactose Substances 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 7
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 206010010904 Convulsion Diseases 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 244000309464 bull Species 0.000 description 3
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- 238000011161 development Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
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- 229910052740 iodine Inorganic materials 0.000 description 3
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- 238000007911 parenteral administration Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
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- 239000012453 solvate Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- MWSPVZXQINZJFP-UHFFFAOYSA-N 2-bromo-2-(4-fluorophenyl)-1-(4-methylsulfonylphenyl)ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C(Br)C1=CC=C(F)C=C1 MWSPVZXQINZJFP-UHFFFAOYSA-N 0.000 description 2
- AZVBUXADPFKFPH-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=CC2=N1 AZVBUXADPFKFPH-UHFFFAOYSA-N 0.000 description 2
- FMIAWMTWGFMXDB-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine-8-carbaldehyde Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=C(C=O)C2=N1 FMIAWMTWGFMXDB-UHFFFAOYSA-N 0.000 description 2
- KDSWLPVULUCPSK-UHFFFAOYSA-N 3-(4-fluorophenyl)-7,8-dimethyl-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound N1=C2C(C)=C(C)C=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 KDSWLPVULUCPSK-UHFFFAOYSA-N 0.000 description 2
- DPJUCZCNHAEIFB-UHFFFAOYSA-N 3-(4-fluorophenyl)-8-methyl-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound N1=C2C(C)=CC=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 DPJUCZCNHAEIFB-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
- FEOWTZPAOVYXOI-UHFFFAOYSA-N 5-bromo-3-(4-fluorophenyl)-8-methyl-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound N1=C2C(C)=CC=C(Br)N2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 FEOWTZPAOVYXOI-UHFFFAOYSA-N 0.000 description 2
- BADBOOQYMBPIGC-UHFFFAOYSA-N 6-bromo-3-(4-fluorophenyl)-8-methyl-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound N1=C2C(C)=CC(Br)=CN2C(C=2C=CC(F)=CC=2)=C1C1=CC=C(S(C)(=O)=O)C=C1 BADBOOQYMBPIGC-UHFFFAOYSA-N 0.000 description 2
- MCEJEBFAGLZXKJ-UHFFFAOYSA-N 8-chloro-3-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(F)=CC=2)N2C=CC=C(Cl)C2=N1 MCEJEBFAGLZXKJ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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- 108090000790 Enzymes Proteins 0.000 description 2
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- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
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- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003153 stable transfection Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000003890 substance P antagonist Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 201000004595 synovitis Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000008215 water for injection Substances 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9506965.4A GB9506965D0 (en) | 1995-04-04 | 1995-04-04 | Chemical compounds |
| GB9506965.4 | 1995-04-04 | ||
| GB9512099.4 | 1995-06-14 | ||
| GBGB9512099.4A GB9512099D0 (en) | 1995-06-14 | 1995-06-14 | Chemical compounds |
| GB9516117.0 | 1995-08-05 | ||
| GBGB9516117.0A GB9516117D0 (en) | 1995-08-05 | 1995-08-05 | Chemical compounds |
| PCT/EP1996/001438 WO1996031509A1 (en) | 1995-04-04 | 1996-04-02 | IMIDAZO[1,2-a]PYRIDINE DERIVATIVES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11501049A true JPH11501049A (ja) | 1999-01-26 |
Family
ID=27267657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8529971A Pending JPH11501049A (ja) | 1995-04-04 | 1996-04-02 | イミダゾ〔１，２−ａ〕ピリジン誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0819127A1 (cs) |
| JP (1) | JPH11501049A (cs) |
| KR (1) | KR19980703559A (cs) |
| CN (1) | CN1186492A (cs) |
| AU (1) | AU5276696A (cs) |
| BG (1) | BG101934A (cs) |
| CA (1) | CA2216809A1 (cs) |
| CZ (1) | CZ313397A3 (cs) |
| EA (1) | EA199700209A1 (cs) |
| HU (1) | HUP9801602A3 (cs) |
| IS (1) | IS4570A (cs) |
| NO (1) | NO974595L (cs) |
| NZ (1) | NZ304886A (cs) |
| PL (1) | PL322623A1 (cs) |
| SK (1) | SK133297A3 (cs) |
| TR (1) | TR199701105T1 (cs) |
| WO (1) | WO1996031509A1 (cs) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2764292B1 (fr) * | 1997-06-10 | 2000-12-29 | Innothera Lab Sa | Utilisation de derives de tetracycles dicetoniques, nouveaux composes obtenus et leur application en therapeutique |
| US6307047B1 (en) | 1997-08-22 | 2001-10-23 | Abbott Laboratories | Prostaglandin endoperoxide H synthase biosynthesis inhibitors |
| US6525053B1 (en) | 1997-08-22 | 2003-02-25 | Abbott Laboratories | Prostaglandin endoperoxide H synthase biosynthesis inhibitors |
| ES2203985T3 (es) | 1997-09-05 | 2004-04-16 | Glaxo Group Limited | Derivados de 2,3-diaril-pirazolo(1,5)piridazina, su preparacion y su uso como inhibidores de la ciclooxigenasa 2(cox-2)`. |
| FR2770131A1 (fr) * | 1997-10-27 | 1999-04-30 | Union Pharma Scient Appl | Nouvelle association pharmaceutique a activite analgesique |
| FR2771005B1 (fr) * | 1997-11-18 | 2002-06-07 | Union Pharma Scient Appl | Nouvelle association pharmaceutique a activite analgesique |
| GB9810920D0 (en) * | 1998-05-21 | 1998-07-22 | Merck Sharp & Dohme | Therapeutic use |
| ES2140354B1 (es) * | 1998-08-03 | 2000-11-01 | S A L V A T Lab Sa | Imidazo (1,2a) azinas sustituidas como inhibidores selectivos de la cox-2. |
| TW587079B (en) * | 1998-09-25 | 2004-05-11 | Almirall Prodesfarma Ag | 2-phenylpyran-4-one derivatives |
| CA2349567A1 (en) * | 1998-11-03 | 2000-05-11 | Glaxo Group Limited | Pyrazolopyridine derivatives as selective cox-2 inhibitors |
| US6498166B1 (en) | 1999-02-27 | 2002-12-24 | Smithkline Beecham Corporation | Pyrazolopyridines |
| NZ513960A (en) | 1999-12-08 | 2004-02-27 | Pharmacia Corp | Cyclooxygenase-2 inhibitor compositions having rapid onset of therapeutic effect |
| GB9930358D0 (en) * | 1999-12-22 | 2000-02-09 | Glaxo Group Ltd | Process for the preparation of chemical compounds |
| WO2001045703A1 (en) | 1999-12-23 | 2001-06-28 | Nitromed, Inc. | Nitrosated and nitrosylated cyclooxygenase-2 inhibitors, compositions and methods of use |
| GB0002312D0 (en) * | 2000-02-01 | 2000-03-22 | Glaxo Group Ltd | Medicaments |
| PE20011333A1 (es) | 2000-03-16 | 2002-01-16 | Almirall Prodesfarma Ag | Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2 |
| PE20020146A1 (es) * | 2000-07-13 | 2002-03-31 | Upjohn Co | Formulacion oftalmica que comprende un inhibidor de ciclooxigenasa-2 (cox-2) |
| ATE366569T1 (de) | 2000-07-20 | 2007-08-15 | Lauras As | Verwendung von cox-2 inhibitoren als immunostimulantien zur behandlung von hiv oder aids |
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| GB0025449D0 (en) * | 2000-10-17 | 2000-11-29 | Glaxo Group Ltd | Chemical compounds |
| AU2002239344A1 (en) | 2000-12-15 | 2002-06-24 | Glaxo Group Limited | Pyrazolopyridines |
| JP2004515550A (ja) | 2000-12-15 | 2004-05-27 | グラクソ グループ リミテッド | 治療用化合物 |
| WO2002072581A2 (en) | 2001-03-08 | 2002-09-19 | Smithkline Beecham Corporation | Pyrazolopyriadine derivatives |
| WO2002078700A1 (en) | 2001-03-30 | 2002-10-10 | Smithkline Beecham Corporation | Pyralopyridines, process for their preparation and use as therapteutic compounds |
| MY137736A (en) | 2001-04-03 | 2009-03-31 | Pharmacia Corp | Reconstitutable parenteral composition |
| WO2002083672A1 (en) | 2001-04-10 | 2002-10-24 | Smithkline Beecham Corporation | Antiviral pyrazolopyridine compounds |
| WO2002088124A2 (en) | 2001-04-27 | 2002-11-07 | Smithkline Beecham Corporation | Pyrazolo'1,5-a!pyridine derivatives |
| US6756498B2 (en) | 2001-04-27 | 2004-06-29 | Smithkline Beecham Corporation | Process for the preparation of chemical compounds |
| CZ20033518A3 (en) | 2001-06-21 | 2004-05-12 | Smithklineábeechamácorporation | Imidazo(1,2-a)pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| AR038957A1 (es) | 2001-08-15 | 2005-02-02 | Pharmacia Corp | Terapia de combinacion para el tratamiento del cancer |
| EP1432712B1 (en) | 2001-10-05 | 2006-05-17 | SmithKline Beecham Corporation | Imidazo-pyridine derivatives for use in the treatment of herpes viral infection |
| GB0124933D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124936D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124939D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124941D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124931D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124934D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124938D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| DE60222465T2 (de) | 2001-12-11 | 2008-06-05 | Smithkline Beecham Corp. | Pyrazolopyridin-derivate als antiherpesmittel |
| DK1474395T3 (da) | 2002-02-12 | 2008-02-11 | Smithkline Beecham Corp | Nicotinamidderivater, der er nyttige som p38-inhibitorer |
| CA2492066A1 (en) | 2002-06-28 | 2004-01-08 | Nitromed, Inc. | Oxime and/or hydrazone containing nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
| US7153863B2 (en) | 2002-10-03 | 2006-12-26 | Smithkline Beecham Corporation | Therapeutic compounds based on pyrazolopyridline derivatives |
| KR20040072004A (ko) | 2003-02-07 | 2004-08-16 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자용 발광 화합물 및 그를 이용한 유기전계발광 소자 |
| GB0308185D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| GB0308186D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| GB0308201D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| CA2519189C (en) | 2003-05-07 | 2012-07-17 | Osteologix A/S | Water-soluble strontium salts for use in treatment of cartilage and/or bone conditions |
| GB0318814D0 (en) | 2003-08-11 | 2003-09-10 | Smithkline Beecham Corp | Novel compounds |
| WO2006041855A2 (en) | 2004-10-04 | 2006-04-20 | Nitromed, Inc. | Compositions and methods using apocynin compounds and nitric oxide donors |
| WO2007016677A2 (en) | 2005-08-02 | 2007-02-08 | Nitromed, Inc. | Nitric oxide enhancing antimicrobial compounds, compositions and methods of use |
| US8067414B2 (en) | 2006-03-29 | 2011-11-29 | Nicox S.A. | Nitric oxide enhancing prostaglandin compounds, compositions and methods of use |
| US7750007B2 (en) | 2006-11-06 | 2010-07-06 | Supergen, Inc. | Imidazo[1,2-beta]pyridazine and pyrazolo[1,5-alpha]pyrimidine derivatives and their use as protein kinase inhibitors |
| WO2013013188A1 (en) | 2011-07-21 | 2013-01-24 | Tolero Pharmaceuticals, Inc. | Heterocyclic protein kinase inhibitors |
| EP3292213A1 (en) | 2015-05-04 | 2018-03-14 | Academisch Medisch Centrum | Biomarkers for the detection of aspirin insensitivity |
| MX2021009371A (es) | 2019-02-12 | 2021-09-10 | Sumitomo Pharma Oncology Inc | Formulaciones que comprenden inhibidores de proteina cinasa heterociclicos. |
| WO2022195579A1 (en) | 2021-03-15 | 2022-09-22 | Saul Yedgar | Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory diseases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3455924A (en) * | 1967-02-08 | 1969-07-15 | Upjohn Co | Dianisylimidazoles |
-
1996
- 1996-04-02 CZ CZ973133A patent/CZ313397A3/cs unknown
- 1996-04-02 SK SK1332-97A patent/SK133297A3/sk unknown
- 1996-04-02 HU HU9801602A patent/HUP9801602A3/hu unknown
- 1996-04-02 AU AU52766/96A patent/AU5276696A/en not_active Abandoned
- 1996-04-02 EA EA199700209A patent/EA199700209A1/ru unknown
- 1996-04-02 TR TR97/01105T patent/TR199701105T1/xx unknown
- 1996-04-02 CN CN96194403A patent/CN1186492A/zh active Pending
- 1996-04-02 WO PCT/EP1996/001438 patent/WO1996031509A1/en not_active Ceased
- 1996-04-02 NZ NZ304886A patent/NZ304886A/en unknown
- 1996-04-02 JP JP8529971A patent/JPH11501049A/ja active Pending
- 1996-04-02 PL PL96322623A patent/PL322623A1/xx unknown
- 1996-04-02 CA CA002216809A patent/CA2216809A1/en not_active Abandoned
- 1996-04-02 KR KR1019970706963A patent/KR19980703559A/ko not_active Ceased
- 1996-04-02 EP EP96909164A patent/EP0819127A1/en not_active Withdrawn
-
1997
- 1997-09-25 IS IS4570A patent/IS4570A/is unknown
- 1997-09-30 BG BG101934A patent/BG101934A/xx unknown
- 1997-10-03 NO NO974595A patent/NO974595L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO974595L (no) | 1997-12-03 |
| KR19980703559A (ko) | 1998-11-05 |
| SK133297A3 (en) | 1998-07-08 |
| HUP9801602A2 (hu) | 1998-11-30 |
| TR199701105T1 (xx) | 1998-02-21 |
| NO974595D0 (no) | 1997-10-03 |
| PL322623A1 (en) | 1998-02-02 |
| HUP9801602A3 (en) | 1999-01-28 |
| NZ304886A (en) | 1998-11-25 |
| AU5276696A (en) | 1996-10-23 |
| IS4570A (is) | 1997-09-25 |
| BG101934A (en) | 1999-04-30 |
| CN1186492A (zh) | 1998-07-01 |
| CZ313397A3 (cs) | 1998-03-18 |
| WO1996031509A1 (en) | 1996-10-10 |
| MX9707379A (es) | 1997-11-29 |
| EP0819127A1 (en) | 1998-01-21 |
| CA2216809A1 (en) | 1996-10-10 |
| EA199700209A1 (ru) | 1998-04-30 |
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