NO872372L - Fremgangsmaate for fremstilling av kondenserte imidazohetero-cykliske forbindelser. - Google Patents
Fremgangsmaate for fremstilling av kondenserte imidazohetero-cykliske forbindelser.Info
- Publication number
- NO872372L NO872372L NO872372A NO872372A NO872372L NO 872372 L NO872372 L NO 872372L NO 872372 A NO872372 A NO 872372A NO 872372 A NO872372 A NO 872372A NO 872372 L NO872372 L NO 872372L
- Authority
- NO
- Norway
- Prior art keywords
- mol
- water
- solid
- imidazo
- room temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- -1 hydroxymethylene Chemical group 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 25
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 150000001408 amides Chemical class 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 150000007513 acids Chemical class 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 163
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 160
- 239000002904 solvent Substances 0.000 claims description 54
- 238000004519 manufacturing process Methods 0.000 claims description 50
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims description 6
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 238000005987 sulfurization reaction Methods 0.000 claims description 3
- 239000003637 basic solution Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 2
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- 239000003158 myorelaxant agent Substances 0.000 abstract description 2
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229940035363 muscle relaxants Drugs 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 515
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 399
- 239000007787 solid Substances 0.000 description 392
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 372
- 229910001868 water Inorganic materials 0.000 description 367
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 324
- 239000000243 solution Substances 0.000 description 297
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 261
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 259
- 239000011541 reaction mixture Substances 0.000 description 234
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 225
- 238000004458 analytical method Methods 0.000 description 218
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 204
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 147
- 239000000203 mixture Substances 0.000 description 139
- 239000000706 filtrate Substances 0.000 description 133
- 238000001914 filtration Methods 0.000 description 131
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 126
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 123
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 78
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 74
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- 239000000725 suspension Substances 0.000 description 71
- 239000010410 layer Substances 0.000 description 70
- 239000011343 solid material Substances 0.000 description 65
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 62
- 239000012299 nitrogen atmosphere Substances 0.000 description 58
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 50
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 50
- 239000003921 oil Substances 0.000 description 50
- 235000019198 oils Nutrition 0.000 description 50
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 50
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 48
- 239000012065 filter cake Substances 0.000 description 48
- LTCYBYUOSOJSJD-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=C(Cl)C=C1 LTCYBYUOSOJSJD-UHFFFAOYSA-N 0.000 description 47
- 239000002244 precipitate Substances 0.000 description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 235000019441 ethanol Nutrition 0.000 description 45
- 238000010992 reflux Methods 0.000 description 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- 238000001953 recrystallisation Methods 0.000 description 35
- 229910052938 sodium sulfate Inorganic materials 0.000 description 35
- 235000011152 sodium sulphate Nutrition 0.000 description 35
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 33
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 32
- 235000019341 magnesium sulphate Nutrition 0.000 description 32
- 239000003208 petroleum Substances 0.000 description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 31
- 230000005587 bubbling Effects 0.000 description 30
- 229910052799 carbon Inorganic materials 0.000 description 28
- 238000001816 cooling Methods 0.000 description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 25
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 24
- 238000009835 boiling Methods 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000013078 crystal Substances 0.000 description 22
- 235000015497 potassium bicarbonate Nutrition 0.000 description 22
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 22
- 239000011736 potassium bicarbonate Substances 0.000 description 22
- JWMHRAUUHFSEJO-UHFFFAOYSA-N ethyl 2-[(3-nitropyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1[N+]([O-])=O JWMHRAUUHFSEJO-UHFFFAOYSA-N 0.000 description 20
- 238000000354 decomposition reaction Methods 0.000 description 19
- 239000012458 free base Substances 0.000 description 18
- 239000011521 glass Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- SHUQVZDDZJLFLH-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=CC(Cl)=C1 SHUQVZDDZJLFLH-UHFFFAOYSA-N 0.000 description 16
- 238000002425 crystallisation Methods 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- FAIHEMXOCGAZCC-UHFFFAOYSA-N 2-[2-(4-bromophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=C(Br)C=C1 FAIHEMXOCGAZCC-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- 229960004132 diethyl ether Drugs 0.000 description 13
- 239000005457 ice water Substances 0.000 description 13
- 239000008188 pellet Substances 0.000 description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 229910000634 wood's metal Inorganic materials 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 238000001556 precipitation Methods 0.000 description 11
- UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 10
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 10
- FEOHNMCVUVSHJA-UHFFFAOYSA-N ethyl 2-[(3-aminopyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1N FEOHNMCVUVSHJA-UHFFFAOYSA-N 0.000 description 10
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 10
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 10
- JPPWUNIENICFBZ-UHFFFAOYSA-N 2-[2-[4-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=C(C(F)(F)F)C=C1 JPPWUNIENICFBZ-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 9
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 8
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 8
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 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 description 7
- 239000012267 brine Substances 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000001263 acyl chlorides Chemical class 0.000 description 6
- 239000002178 crystalline material Substances 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 6
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 6
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- WDPISXCGMFKLML-UHFFFAOYSA-N 2-(2-pyridin-2-ylimidazo[4,5-b]pyridin-3-yl)acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=CC=N1 WDPISXCGMFKLML-UHFFFAOYSA-N 0.000 description 5
- JMTTXBKHYYLZOM-UHFFFAOYSA-N 2-[(3-nitropyridin-2-yl)amino]acetamide Chemical compound NC(=O)CNC1=NC=CC=C1[N+]([O-])=O JMTTXBKHYYLZOM-UHFFFAOYSA-N 0.000 description 5
- OXOWIQTYRUEQPJ-UHFFFAOYSA-N 2-[2-(3-bromophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=CC(Br)=C1 OXOWIQTYRUEQPJ-UHFFFAOYSA-N 0.000 description 5
- SFFQMYWMUBFXKK-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=CN=C2N1CC(O)=O SFFQMYWMUBFXKK-UHFFFAOYSA-N 0.000 description 5
- OXOUQFGMKIMPKX-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]propanoic acid Chemical compound N=1C2=CC=CN=C2N(CCC(=O)O)C=1C1=CC=C(Cl)C=C1 OXOUQFGMKIMPKX-UHFFFAOYSA-N 0.000 description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
- 230000003311 flocculating effect Effects 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- LSFZJGQFSJEDGF-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid Chemical compound N=1C2=CC=CN=C2N(CC(=O)O)C=1C1=CC=C(Cl)C(Cl)=C1 LSFZJGQFSJEDGF-UHFFFAOYSA-N 0.000 description 4
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
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- QXPDZDILEVKSOS-UHFFFAOYSA-N ethyl 2-[(6-chloro-3-nitropyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC(Cl)=CC=C1[N+]([O-])=O QXPDZDILEVKSOS-UHFFFAOYSA-N 0.000 description 2
- YMUKCHUOTZASKI-UHFFFAOYSA-N ethyl 2-[(6-methoxy-3-nitropyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC(OC)=CC=C1[N+]([O-])=O YMUKCHUOTZASKI-UHFFFAOYSA-N 0.000 description 2
- DIMFMYKPOPSSFY-UHFFFAOYSA-N ethyl 2-[(6-methyl-3-nitropyridin-2-yl)amino]acetate Chemical compound CCOC(=O)CNC1=NC(C)=CC=C1[N+]([O-])=O DIMFMYKPOPSSFY-UHFFFAOYSA-N 0.000 description 2
- ZUUUKTOPYGXELE-UHFFFAOYSA-N ethyl 2-[2-(2-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC=CC=C1Cl ZUUUKTOPYGXELE-UHFFFAOYSA-N 0.000 description 2
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- NCRHULYHNNTUNM-UHFFFAOYSA-N ethyl 2-[2-(3-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC=CC(Cl)=C1 NCRHULYHNNTUNM-UHFFFAOYSA-N 0.000 description 2
- OJZHDUHDBFUDBR-UHFFFAOYSA-N ethyl 2-[2-(4-bromophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC=C(Br)C=C1 OJZHDUHDBFUDBR-UHFFFAOYSA-N 0.000 description 2
- YDHLOYXHIPKIOF-UHFFFAOYSA-N ethyl 2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC=C(Cl)C=C1 YDHLOYXHIPKIOF-UHFFFAOYSA-N 0.000 description 2
- ANKPCGXGPYJRPP-UHFFFAOYSA-N ethyl 2-[2-(4-chloropyridin-2-yl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OCC)C=1C1=CC(Cl)=CC=N1 ANKPCGXGPYJRPP-UHFFFAOYSA-N 0.000 description 2
- FOLKHXDSCLCHKB-UHFFFAOYSA-N ethyl 2-[[2-(diethylamino)-6-methyl-3-nitropyridin-4-yl]amino]acetate Chemical compound CCOC(=O)CNC1=CC(C)=NC(N(CC)CC)=C1[N+]([O-])=O FOLKHXDSCLCHKB-UHFFFAOYSA-N 0.000 description 2
- QYTRJJOYBWKWDC-UHFFFAOYSA-N ethyl 2-[[2-[2-(3-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetyl]amino]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)NCC(=O)OCC)C=1C1=CC=CC(Cl)=C1 QYTRJJOYBWKWDC-UHFFFAOYSA-N 0.000 description 2
- CBPLTBPMGINJCK-UHFFFAOYSA-N ethyl 2-[[3-(pyridine-2-carbonylamino)pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=N1 CBPLTBPMGINJCK-UHFFFAOYSA-N 0.000 description 2
- PMFVRGZNHBYNHJ-UHFFFAOYSA-N ethyl 2-[[3-[(2-chlorobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=C1Cl PMFVRGZNHBYNHJ-UHFFFAOYSA-N 0.000 description 2
- MFJQASCYUJILAX-UHFFFAOYSA-N ethyl 2-[[3-[(2-methoxybenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=C1OC MFJQASCYUJILAX-UHFFFAOYSA-N 0.000 description 2
- NOWNMJOJLPQMLB-UHFFFAOYSA-N ethyl 2-[[3-[(3-chlorobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC(Cl)=C1 NOWNMJOJLPQMLB-UHFFFAOYSA-N 0.000 description 2
- VYSOQIKAHVVYQB-UHFFFAOYSA-N ethyl 2-[[3-[(3-fluorobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC(F)=C1 VYSOQIKAHVVYQB-UHFFFAOYSA-N 0.000 description 2
- RHEZUULXGCTBLA-UHFFFAOYSA-N ethyl 2-[[3-[(4-bromobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=C(Br)C=C1 RHEZUULXGCTBLA-UHFFFAOYSA-N 0.000 description 2
- QWAIWRSSWLSZQY-UHFFFAOYSA-N ethyl 2-[[3-[(4-chlorobenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=C(Cl)C=C1 QWAIWRSSWLSZQY-UHFFFAOYSA-N 0.000 description 2
- UXCMTYHWVLACKB-UHFFFAOYSA-N ethyl 2-[[3-[(4-methoxybenzoyl)amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=C(OC)C=C1 UXCMTYHWVLACKB-UHFFFAOYSA-N 0.000 description 2
- FRPDDMHNNCIWIS-UHFFFAOYSA-N ethyl 2-[[3-[[3-(trifluoromethyl)benzoyl]amino]pyridin-2-yl]amino]acetate Chemical compound CCOC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 FRPDDMHNNCIWIS-UHFFFAOYSA-N 0.000 description 2
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- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
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- TZIRGFLJBVMCRK-UHFFFAOYSA-N n,n-dimethyl-2-[2-[3-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide Chemical compound N=1C2=CC=CN=C2N(CC(=O)N(C)C)C=1C1=CC=CC(C(F)(F)F)=C1 TZIRGFLJBVMCRK-UHFFFAOYSA-N 0.000 description 1
- DMLVWFJFBBVYIJ-UHFFFAOYSA-N n,n-dimethyl-2-[2-[4-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide Chemical compound N=1C2=CC=CN=C2N(CC(=O)N(C)C)C=1C1=CC=C(C(F)(F)F)C=C1 DMLVWFJFBBVYIJ-UHFFFAOYSA-N 0.000 description 1
- LDPVOCLLMPQTDG-UHFFFAOYSA-N n,n-dipropyl-2-[2-[4-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide Chemical compound N=1C2=CC=CN=C2N(CC(=O)N(CCC)CCC)C=1C1=CC=C(C(F)(F)F)C=C1 LDPVOCLLMPQTDG-UHFFFAOYSA-N 0.000 description 1
- ZFJDMHUEULLLKQ-UHFFFAOYSA-N n-(2-acetamidoethyl)-2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetamide;hydrate Chemical compound O.N=1C2=CC=CN=C2N(CC(=O)NCCNC(=O)C)C=1C1=CC=C(Cl)C=C1 ZFJDMHUEULLLKQ-UHFFFAOYSA-N 0.000 description 1
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
- DOCXSTCEEOJAIQ-UHFFFAOYSA-N n-(2-chlorophenyl)-2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC=CN=C2N1CC(=O)NC1=CC=CC=C1Cl DOCXSTCEEOJAIQ-UHFFFAOYSA-N 0.000 description 1
- AIFPVYWYLOJPOV-UHFFFAOYSA-N n-[2-[(2-amino-2-oxoethyl)amino]pyridin-3-yl]-2-chlorobenzamide Chemical compound NC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=C1Cl AIFPVYWYLOJPOV-UHFFFAOYSA-N 0.000 description 1
- VOHDXYOSABECBZ-UHFFFAOYSA-N n-[2-[(2-amino-2-oxoethyl)amino]pyridin-3-yl]-2-chlorobenzamide;hydrochloride Chemical compound Cl.NC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=C1Cl VOHDXYOSABECBZ-UHFFFAOYSA-N 0.000 description 1
- NKZQCJMAMAEOSD-UHFFFAOYSA-N n-[2-[(2-amino-2-oxoethyl)amino]pyridin-3-yl]-3-chlorobenzamide Chemical compound NC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC(Cl)=C1 NKZQCJMAMAEOSD-UHFFFAOYSA-N 0.000 description 1
- VUCAAJCVXUGJEC-UHFFFAOYSA-N n-[2-[(2-amino-2-oxoethyl)amino]pyridin-3-yl]-4-chlorobenzamide Chemical compound NC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=C(Cl)C=C1 VUCAAJCVXUGJEC-UHFFFAOYSA-N 0.000 description 1
- VOZIMSIDSUWBRF-UHFFFAOYSA-N n-[2-[(2-amino-2-oxoethyl)amino]pyridin-3-yl]pyridine-2-carboxamide Chemical compound NC(=O)CNC1=NC=CC=C1NC(=O)C1=CC=CC=N1 VOZIMSIDSUWBRF-UHFFFAOYSA-N 0.000 description 1
- MRGZZCYPLCEJPP-UHFFFAOYSA-N n-benzyl-2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]-n-methylacetamide Chemical compound C=1C=C(Cl)C=CC=1C1=NC2=CC=CN=C2N1CC(=O)N(C)CC1=CC=CC=C1 MRGZZCYPLCEJPP-UHFFFAOYSA-N 0.000 description 1
- KXTVAIVXNLGUCO-UHFFFAOYSA-N n-benzyl-2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC=CN=C2N1CC(=O)NCC1=CC=CC=C1 KXTVAIVXNLGUCO-UHFFFAOYSA-N 0.000 description 1
- OBOIRDKITDTDSW-UHFFFAOYSA-N n-benzyl-2-[2-[4-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC2=CC=CN=C2N1CC(=O)NCC1=CC=CC=C1 OBOIRDKITDTDSW-UHFFFAOYSA-N 0.000 description 1
- OTAUZKVOFLRTOJ-UHFFFAOYSA-N n-benzyl-n-methyl-2-[2-[4-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide;hydrate Chemical compound O.C=1C=C(C(F)(F)F)C=CC=1C1=NC2=CC=CN=C2N1CC(=O)N(C)CC1=CC=CC=C1 OTAUZKVOFLRTOJ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- MGZSVLIVUKTFIM-UHFFFAOYSA-N n-methyl-2-(2-pyridin-2-ylimidazo[4,5-b]pyridin-3-yl)acetamide Chemical compound N=1C2=CC=CN=C2N(CC(=O)NC)C=1C1=CC=CC=N1 MGZSVLIVUKTFIM-UHFFFAOYSA-N 0.000 description 1
- HUGARFACUNSTSF-UHFFFAOYSA-N n-methyl-3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound CNCCCN1CCN(C)CC1 HUGARFACUNSTSF-UHFFFAOYSA-N 0.000 description 1
- VIPUDQNHLTVLRS-UHFFFAOYSA-N n-methyl-n-phenyl-2-[2-[4-(trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CN(C1=NC=CC=C1N=1)C=1C1=CC=C(C(F)(F)F)C=C1 VIPUDQNHLTVLRS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- DQKDEGTVXPKTIJ-UHFFFAOYSA-M potassium 4-[[2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetyl]amino]butanoate hydrate Chemical compound O.[K+].[O-]C(=O)CCCNC(=O)Cn1c(nc2cccnc12)-c1ccc(Cl)cc1 DQKDEGTVXPKTIJ-UHFFFAOYSA-M 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- XCLOGPDGWIDLEM-UHFFFAOYSA-N tert-butyl 2-(2-pyridin-2-ylimidazo[4,5-b]pyridin-3-yl)acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OC(C)(C)C)C=1C1=CC=CC=N1 XCLOGPDGWIDLEM-UHFFFAOYSA-N 0.000 description 1
- QCPYBCJICYNWNG-UHFFFAOYSA-N tert-butyl 2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]acetate Chemical compound N=1C2=CC=CN=C2N(CC(=O)OC(C)(C)C)C=1C1=CC=C(Cl)C=C1 QCPYBCJICYNWNG-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/871,772 US4772600A (en) | 1986-06-09 | 1986-06-09 | Fused imidazoheterocyclic compounds and pharmaceutical compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
NO872372D0 NO872372D0 (no) | 1987-06-05 |
NO872372L true NO872372L (no) | 1987-12-10 |
Family
ID=25358086
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO872372A NO872372L (no) | 1986-06-09 | 1987-06-05 | Fremgangsmaate for fremstilling av kondenserte imidazohetero-cykliske forbindelser. |
Country Status (18)
Country | Link |
---|---|
US (1) | US4772600A (da) |
EP (1) | EP0255217B1 (da) |
JP (1) | JPS62292782A (da) |
KR (1) | KR950014568B1 (da) |
AT (1) | ATE71945T1 (da) |
AU (1) | AU609720B2 (da) |
CA (1) | CA1295329C (da) |
DE (1) | DE3776220D1 (da) |
DK (1) | DK288787A (da) |
FI (1) | FI872566A (da) |
HU (1) | HU199466B (da) |
IE (1) | IE60628B1 (da) |
IL (1) | IL82574A (da) |
NO (1) | NO872372L (da) |
NZ (1) | NZ220259A (da) |
PH (1) | PH24262A (da) |
PT (1) | PT85054B (da) |
ZA (1) | ZA873783B (da) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0517812A4 (en) * | 1990-02-13 | 1995-10-18 | Merck & Co Inc | Angiotensin ii antagonists incorporating a substituted benzyl element |
US5066654A (en) * | 1990-10-22 | 1991-11-19 | A. H. Robins Company, Incorporated | 2-aryl-3-heterocyclicmethyl-3H-imidazo[4,5-b]pyridines as anxiolytics and anticonvulsants |
DK1221444T3 (da) * | 1999-07-02 | 2005-11-14 | Eisai Co Ltd | Kondenserede imidazolforbindelser og lægemidler mod diabetes mellitus |
US7589199B2 (en) | 2002-06-12 | 2009-09-15 | Chemocentryx, Inc. | Substituted piperazines |
US20050256130A1 (en) * | 2002-06-12 | 2005-11-17 | Chemocentryx, Inc. | Substituted piperazines |
WO2009158118A2 (en) * | 2008-05-30 | 2009-12-30 | University Of Notre Dame Du Lac | Anti-bacterial agents from benzo[d]heterocyclic scaffolds for prevention and treatment of multidrug resistant bacteria |
AR099677A1 (es) * | 2014-03-07 | 2016-08-10 | Sumitomo Chemical Co | Compuesto heterocíclico fusionado y su uso para el control de plagas |
HUE050562T2 (hu) * | 2014-12-17 | 2020-12-28 | Syngenta Participations Ag | Pezticid hatású heterociklus-származékok kéntartalmú szubsztituensekkel |
CN113004252B (zh) * | 2019-12-20 | 2023-06-09 | 江苏先声药业有限公司 | 一种芳基并咪唑类衍生物及其用途 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE788065A (fr) * | 1971-08-26 | 1973-02-26 | Degussa | Nouvelles aza-benzimidazoles et procede pour leur preparation |
DE2305339C3 (de) * | 1973-02-03 | 1980-05-08 | Dr. Karl Thomae Gmbh, 7950 Biberach | Imidazo [4,5-b] pyridine, ihre Herstellung und ihre Verwendung als Cardiötonica |
FI58126C (fi) * | 1973-02-03 | 1980-12-10 | Thomae Gmbh Dr K | Foerfarande foer framstaellning av kardiotona och blodtryckssaenkande 2-fenyl-1h-imidatso(4,5-b)pyridiner |
ES473201A1 (es) * | 1977-09-26 | 1979-03-16 | Degussa | Procedimiento para la preparacion de 7-azabencimidazoles |
FR2525601A1 (fr) * | 1982-04-21 | 1983-10-28 | Synthelabo | Derives d'imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
GB8307865D0 (en) * | 1983-03-22 | 1983-04-27 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
DE3673544D1 (de) * | 1985-03-27 | 1990-09-27 | Merck & Co Inc | 3-nitropyridinderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel. |
NZ217755A (en) * | 1985-10-09 | 1989-08-29 | Chemie Linz Ag | 2-(2-thienyl)-imidazo(4,5-c)pyridine derivatives and pharmaceutical compositions |
-
1986
- 1986-06-09 US US06/871,772 patent/US4772600A/en not_active Expired - Lifetime
-
1987
- 1987-05-11 NZ NZ220259A patent/NZ220259A/en unknown
- 1987-05-19 IL IL82574A patent/IL82574A/xx unknown
- 1987-05-26 ZA ZA873783A patent/ZA873783B/xx unknown
- 1987-06-02 PH PH35337A patent/PH24262A/en unknown
- 1987-06-04 AU AU73830/87A patent/AU609720B2/en not_active Ceased
- 1987-06-04 DK DK288787A patent/DK288787A/da not_active Application Discontinuation
- 1987-06-05 IE IE149087A patent/IE60628B1/en not_active IP Right Cessation
- 1987-06-05 NO NO872372A patent/NO872372L/no unknown
- 1987-06-08 CA CA000539043A patent/CA1295329C/en not_active Expired - Fee Related
- 1987-06-08 KR KR1019870005781A patent/KR950014568B1/ko active IP Right Grant
- 1987-06-08 FI FI872566A patent/FI872566A/fi not_active Application Discontinuation
- 1987-06-08 HU HU872617A patent/HU199466B/hu not_active IP Right Cessation
- 1987-06-09 EP EP87305078A patent/EP0255217B1/en not_active Expired - Lifetime
- 1987-06-09 PT PT85054A patent/PT85054B/pt not_active IP Right Cessation
- 1987-06-09 AT AT87305078T patent/ATE71945T1/de not_active IP Right Cessation
- 1987-06-09 JP JP62143961A patent/JPS62292782A/ja active Pending
- 1987-06-09 DE DE8787305078T patent/DE3776220D1/de not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
IE871490L (en) | 1987-12-09 |
EP0255217A1 (en) | 1988-02-03 |
ZA873783B (en) | 1988-04-27 |
HU199466B (en) | 1990-02-28 |
DK288787D0 (da) | 1987-06-04 |
DK288787A (da) | 1987-12-10 |
ATE71945T1 (de) | 1992-02-15 |
KR880000438A (ko) | 1988-03-25 |
EP0255217B1 (en) | 1992-01-22 |
PH24262A (en) | 1990-05-29 |
AU7383087A (en) | 1987-12-10 |
JPS62292782A (ja) | 1987-12-19 |
IL82574A0 (en) | 1987-11-30 |
NO872372D0 (no) | 1987-06-05 |
IE60628B1 (en) | 1994-07-27 |
NZ220259A (en) | 1990-04-26 |
FI872566A0 (fi) | 1987-06-08 |
PT85054B (pt) | 1990-03-08 |
PT85054A (en) | 1987-07-01 |
IL82574A (en) | 1993-05-13 |
KR950014568B1 (ko) | 1995-12-08 |
FI872566A (fi) | 1987-12-10 |
AU609720B2 (en) | 1991-05-09 |
CA1295329C (en) | 1992-02-04 |
DE3776220D1 (de) | 1992-03-05 |
HUT44545A (en) | 1988-03-28 |
US4772600A (en) | 1988-09-20 |
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