CA2770873A1 - Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation - Google Patents
Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation Download PDFInfo
- Publication number
- CA2770873A1 CA2770873A1 CA2770873A CA2770873A CA2770873A1 CA 2770873 A1 CA2770873 A1 CA 2770873A1 CA 2770873 A CA2770873 A CA 2770873A CA 2770873 A CA2770873 A CA 2770873A CA 2770873 A1 CA2770873 A1 CA 2770873A1
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- CA
- Canada
- Prior art keywords
- compound
- mmol
- methyl
- pyridazin
- alkyl
- 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.)
- Abandoned
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- -1 Heterocyclic hydrazone compounds Chemical class 0.000 title description 185
- 206010028980 Neoplasm Diseases 0.000 title description 34
- 201000011510 cancer Diseases 0.000 title description 17
- 206010061218 Inflammation Diseases 0.000 title description 2
- 230000004054 inflammatory process Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 497
- 238000000034 method Methods 0.000 claims abstract description 258
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 79
- 150000003839 salts Chemical class 0.000 claims abstract description 68
- 201000010099 disease Diseases 0.000 claims abstract description 53
- 238000011282 treatment Methods 0.000 claims abstract description 51
- 239000003814 drug Substances 0.000 claims abstract description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 230000001404 mediated effect Effects 0.000 claims abstract description 13
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 12
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 229910052805 deuterium Inorganic materials 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 15
- 229940124597 therapeutic agent Drugs 0.000 claims description 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 230000002062 proliferating effect Effects 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
- 230000004968 inflammatory condition Effects 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 3
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 3
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 2
- 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 241001465754 Metazoa Species 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 215
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 190
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 180
- 239000000243 solution Substances 0.000 description 160
- 238000005160 1H NMR spectroscopy Methods 0.000 description 141
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 121
- 239000007787 solid Substances 0.000 description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 239000000203 mixture Substances 0.000 description 95
- 230000015572 biosynthetic process Effects 0.000 description 90
- 238000003786 synthesis reaction Methods 0.000 description 89
- 229910001868 water Inorganic materials 0.000 description 73
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
- 230000000694 effects Effects 0.000 description 67
- 239000000543 intermediate Substances 0.000 description 65
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 64
- 229910052938 sodium sulfate Inorganic materials 0.000 description 63
- 235000011152 sodium sulphate Nutrition 0.000 description 63
- 239000007832 Na2SO4 Substances 0.000 description 62
- 239000011541 reaction mixture Substances 0.000 description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- 235000019439 ethyl acetate Nutrition 0.000 description 55
- 239000002904 solvent Substances 0.000 description 55
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 49
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000012044 organic layer Substances 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- 239000000460 chlorine Chemical group 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
- 230000002829 reductive effect Effects 0.000 description 32
- 101150041968 CDC13 gene Proteins 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
- 239000012043 crude product Substances 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 239000003112 inhibitor Substances 0.000 description 26
- 208000035475 disorder Diseases 0.000 description 25
- 230000002401 inhibitory effect Effects 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 24
- 239000012267 brine Substances 0.000 description 23
- 238000003818 flash chromatography Methods 0.000 description 23
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
- 230000007423 decrease Effects 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 230000003247 decreasing effect Effects 0.000 description 20
- 235000017557 sodium bicarbonate Nutrition 0.000 description 20
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
- 230000008685 targeting Effects 0.000 description 20
- GNHNBAKYBWJJNF-YIXHJXPBSA-N n-[(e)-(2,4,6-trifluorophenyl)methylideneamino]methanamine Chemical compound CN\N=C\C1=C(F)C=C(F)C=C1F GNHNBAKYBWJJNF-YIXHJXPBSA-N 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- ZKDFGKWZSLHAHN-UHFFFAOYSA-N 1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethanone Chemical compound C1=CN=C2C=C(F)C(CC3=CN=C4C=CC(=NN43)C(=O)C)=CC2=C1 ZKDFGKWZSLHAHN-UHFFFAOYSA-N 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 17
- 229940079593 drug Drugs 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 238000010898 silica gel chromatography Methods 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 15
- 108090000623 proteins and genes Proteins 0.000 description 15
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 14
- 108091000080 Phosphotransferase Proteins 0.000 description 14
- 102000020233 phosphotransferase Human genes 0.000 description 14
- 102000004169 proteins and genes Human genes 0.000 description 14
- 230000001225 therapeutic effect Effects 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- MQWFFAABAAZNMB-UHFFFAOYSA-N 1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]ethanone Chemical compound N1=CC=CC2=CC(CN3N=NC4=NC=C(N=C43)C(=O)C)=CC=C21 MQWFFAABAAZNMB-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- VSHRKGLXEAWCKI-UHFFFAOYSA-N n'-(6-chloropyridazin-3-yl)-2-quinolin-6-ylacetohydrazide Chemical compound N1=NC(Cl)=CC=C1NNC(=O)CC1=CC=C(N=CC=C2)C2=C1 VSHRKGLXEAWCKI-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000005557 antagonist Substances 0.000 description 11
- 150000002431 hydrogen Chemical group 0.000 description 11
- 229910052740 iodine Inorganic materials 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 238000010348 incorporation Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- QCNYMKCQVLOAOU-UHFFFAOYSA-N 1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethanone Chemical compound C1=CN=C2C=C(F)C(CN3N=NC4=NC=C(N=C43)C(=O)C)=CC2=C1 QCNYMKCQVLOAOU-UHFFFAOYSA-N 0.000 description 9
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000002246 antineoplastic agent Substances 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 229910052801 chlorine Chemical group 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000001028 anti-proliverative effect Effects 0.000 description 8
- 229940088679 drug related substance Drugs 0.000 description 8
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 229940086542 triethylamine Drugs 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 7
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 7
- 238000002560 therapeutic procedure Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
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- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 6
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- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 5
- FNMFKKARXKABHH-UHFFFAOYSA-N 1-[3-[difluoro(quinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethanone Chemical compound N1=CC=CC2=CC(C(F)(F)C3=NN=C4C=CC(=NN43)C(=O)C)=CC=C21 FNMFKKARXKABHH-UHFFFAOYSA-N 0.000 description 5
- UETMPFPCEQBDIU-UHFFFAOYSA-N 6-[(5-bromotriazolo[4,5-b]pyrazin-3-yl)methyl]quinoline Chemical compound N1=CC=CC2=CC(CN3N=NC4=NC=C(N=C43)Br)=CC=C21 UETMPFPCEQBDIU-UHFFFAOYSA-N 0.000 description 5
- WYUDQEUQUMBLRF-UHFFFAOYSA-N 6-chloroimidazo[1,2-b]pyridazine-3-carbaldehyde Chemical compound N1=C(Cl)C=CC2=NC=C(C=O)N21 WYUDQEUQUMBLRF-UHFFFAOYSA-N 0.000 description 5
- MXHXHJCXWSYDQO-UHFFFAOYSA-N 7-fluoroquinoline-6-carbaldehyde Chemical compound C1=CC=C2C=C(C=O)C(F)=CC2=N1 MXHXHJCXWSYDQO-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
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- 229960000241 vandetanib Drugs 0.000 description 1
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- YTZALCGQUPRCGW-ZSFNYQMMSA-N verteporfin Chemical compound N1C(C=C2C(=C(CCC(O)=O)C(C=C3C(CCC(=O)OC)=C(C)C(N3)=C3)=N2)C)=C(C=C)C(C)=C1C=C1C2=CC=C(C(=O)OC)[C@@H](C(=O)OC)[C@@]2(C)C3=N1 YTZALCGQUPRCGW-ZSFNYQMMSA-N 0.000 description 1
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- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23332809P | 2009-08-12 | 2009-08-12 | |
| US61/233,328 | 2009-08-12 | ||
| CNPCT/CN2010/071981 | 2010-04-21 | ||
| CN2010071981 | 2010-04-21 | ||
| CNPCT/CN2010/074078 | 2010-06-18 | ||
| CN2010074078 | 2010-06-18 | ||
| PCT/EP2010/061609 WO2011018454A1 (en) | 2009-08-12 | 2010-08-10 | Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2770873A1 true CA2770873A1 (en) | 2011-02-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2770873A Abandoned CA2770873A1 (en) | 2009-08-12 | 2010-08-10 | Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8497368B2 (enExample) |
| EP (1) | EP2464649A1 (enExample) |
| JP (1) | JP5781510B2 (enExample) |
| KR (1) | KR20120089643A (enExample) |
| AU (1) | AU2010283806A1 (enExample) |
| BR (1) | BR112012003262A8 (enExample) |
| CA (1) | CA2770873A1 (enExample) |
| EA (1) | EA201200260A1 (enExample) |
| MX (1) | MX2012001838A (enExample) |
| WO (1) | WO2011018454A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2012002179A (es) | 2009-08-20 | 2012-03-16 | Novartis Ag | Compuestos heterociclicos de oxima. |
| RS61281B1 (sr) * | 2009-12-31 | 2021-02-26 | Hutchison Medipharma Ltd | Sintetički intermedijer koristan u pripremi triazolopiridinskih c-met inhibitora |
| EP3450432A1 (en) | 2010-05-17 | 2019-03-06 | Incozen Therapeutics Pvt. Ltd. | Novel 3,5-disubstitued-3h-imidazo[4,5-b]pyridine and 3,5- disubstitued - 3h-[1,2,3]triazolo[4,5-b] pyridine compounds as modulators of protein kinases |
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-
2010
- 2010-08-10 EA EA201200260A patent/EA201200260A1/ru unknown
- 2010-08-10 AU AU2010283806A patent/AU2010283806A1/en not_active Abandoned
- 2010-08-10 BR BR112012003262A patent/BR112012003262A8/pt not_active Application Discontinuation
- 2010-08-10 CA CA2770873A patent/CA2770873A1/en not_active Abandoned
- 2010-08-10 MX MX2012001838A patent/MX2012001838A/es not_active Application Discontinuation
- 2010-08-10 WO PCT/EP2010/061609 patent/WO2011018454A1/en not_active Ceased
- 2010-08-10 US US13/389,912 patent/US8497368B2/en not_active Expired - Fee Related
- 2010-08-10 KR KR1020127006238A patent/KR20120089643A/ko not_active Withdrawn
- 2010-08-10 JP JP2012524218A patent/JP5781510B2/ja not_active Expired - Fee Related
- 2010-08-10 EP EP10744553A patent/EP2464649A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012003262A2 (pt) | 2016-03-01 |
| EP2464649A1 (en) | 2012-06-20 |
| US20120142681A1 (en) | 2012-06-07 |
| KR20120089643A (ko) | 2012-08-13 |
| BR112012003262A8 (pt) | 2016-05-17 |
| WO2011018454A1 (en) | 2011-02-17 |
| AU2010283806A1 (en) | 2012-03-01 |
| EA201200260A1 (ru) | 2012-09-28 |
| MX2012001838A (es) | 2012-02-29 |
| JP5781510B2 (ja) | 2015-09-24 |
| US8497368B2 (en) | 2013-07-30 |
| JP2013501749A (ja) | 2013-01-17 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20140812 |