CA2771432A1 - Heterocyclic oxime compounds - Google Patents
Heterocyclic oxime compounds Download PDFInfo
- Publication number
- CA2771432A1 CA2771432A1 CA2771432A CA2771432A CA2771432A1 CA 2771432 A1 CA2771432 A1 CA 2771432A1 CA 2771432 A CA2771432 A CA 2771432A CA 2771432 A CA2771432 A CA 2771432A CA 2771432 A1 CA2771432 A1 CA 2771432A1
- Authority
- CA
- Canada
- Prior art keywords
- mmol
- cndot
- alkyl
- methyl
- compound
- 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
Links
- -1 Heterocyclic oxime compounds Chemical class 0.000 title claims description 170
- 150000001875 compounds Chemical class 0.000 claims abstract description 499
- 238000000034 method Methods 0.000 claims abstract description 267
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 79
- 150000003839 salts Chemical class 0.000 claims abstract description 74
- 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
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 12
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 12
- 230000001404 mediated effect Effects 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 229910052805 deuterium Inorganic materials 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 229940124597 therapeutic agent Drugs 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000013543 active substance Substances 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 230000002062 proliferating effect Effects 0.000 claims description 11
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- IVGLGVJCVDBHBJ-UHFFFAOYSA-N CC=NOCCO Chemical compound CC=NOCCO IVGLGVJCVDBHBJ-UHFFFAOYSA-N 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 3
- 125000003566 oxetanyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 294
- 239000000243 solution Substances 0.000 description 205
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 184
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 172
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 154
- 238000005160 1H NMR spectroscopy Methods 0.000 description 141
- 239000000543 intermediate Substances 0.000 description 120
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 117
- 239000000203 mixture Substances 0.000 description 107
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 102
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 94
- 235000019439 ethyl acetate Nutrition 0.000 description 91
- 239000007787 solid Substances 0.000 description 82
- 229910001868 water Inorganic materials 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
- 239000002904 solvent Substances 0.000 description 78
- 239000007832 Na2SO4 Substances 0.000 description 67
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 67
- 229910052938 sodium sulfate Inorganic materials 0.000 description 67
- 235000011152 sodium sulphate Nutrition 0.000 description 67
- 230000000694 effects Effects 0.000 description 64
- 230000015572 biosynthetic process Effects 0.000 description 62
- 238000003786 synthesis reaction Methods 0.000 description 62
- 239000012044 organic layer Substances 0.000 description 58
- 101150041968 CDC13 gene Proteins 0.000 description 57
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 57
- 239000011541 reaction mixture Substances 0.000 description 54
- 230000002829 reductive effect Effects 0.000 description 50
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 239000000741 silica gel Substances 0.000 description 34
- 229910002027 silica gel Inorganic materials 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 206010028980 Neoplasm Diseases 0.000 description 32
- 239000012267 brine Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 32
- 238000004440 column chromatography Methods 0.000 description 32
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
- 239000012043 crude product Substances 0.000 description 30
- 238000003818 flash chromatography Methods 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
- IIOMIXQUKPORSZ-UHFFFAOYSA-N 6-[(6-bromoimidazo[1,2-a]pyrimidin-3-yl)methyl]quinoline Chemical compound N1=CC=CC2=CC(CC3=CN=C4N=CC(=CN43)Br)=CC=C21 IIOMIXQUKPORSZ-UHFFFAOYSA-N 0.000 description 25
- 208000035475 disorder Diseases 0.000 description 25
- 239000003112 inhibitor Substances 0.000 description 25
- 230000002401 inhibitory effect Effects 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 230000007423 decrease Effects 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 230000003247 decreasing effect Effects 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- 230000008685 targeting Effects 0.000 description 20
- 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 19
- 239000000460 chlorine Chemical group 0.000 description 19
- HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 17
- 229940079593 drug Drugs 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 201000011510 cancer Diseases 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 14
- 229910052740 iodine Inorganic materials 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 230000001225 therapeutic effect Effects 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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 13
- 239000000047 product Substances 0.000 description 13
- 102000004169 proteins and genes Human genes 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 12
- 150000002923 oximes Chemical class 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- QEWBLEMJAWTJOO-UHFFFAOYSA-N 1-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethanone Chemical compound N1=CC=CC2=CC(CC3=NN=C4C=CC(=NN43)C(=O)C)=CC=C21 QEWBLEMJAWTJOO-UHFFFAOYSA-N 0.000 description 11
- MVAXDJWUDYBAAH-UHFFFAOYSA-N 2-aminooxyethanol;hydrochloride Chemical compound Cl.NOCCO MVAXDJWUDYBAAH-UHFFFAOYSA-N 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 239000005557 antagonist Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000010348 incorporation Methods 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- FKDCFTCWGQQZSP-WYMPLXKRSA-N 2-[(e)-1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]oxyethanamine Chemical compound N1=CC=CC2=CC(CN3N=NC4=NC=C(N=C43)C(=N/OCCN)/C)=CC=C21 FKDCFTCWGQQZSP-WYMPLXKRSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 230000002378 acidificating effect Effects 0.000 description 9
- 239000002246 antineoplastic agent Substances 0.000 description 9
- 229910052801 chlorine Chemical group 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical class C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 108091000080 Phosphotransferase Proteins 0.000 description 8
- 230000001028 anti-proliverative effect Effects 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 229940088679 drug related substance Drugs 0.000 description 8
- 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 8
- 102000020233 phosphotransferase Human genes 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 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 7
- ASKREEJRSDOYKI-KKMKTNMSSA-N 2-[(e)-1-[3-[1-(5,7-difluoroquinolin-6-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxyethanol Chemical compound N1=CC=CC2=C(F)C(C(C=3N4N=C(C=CC4=NN=3)C(\C)=N\OCCO)C)=C(F)C=C21 ASKREEJRSDOYKI-KKMKTNMSSA-N 0.000 description 7
- 229910004373 HOAc Inorganic materials 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 7
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 238000002560 therapeutic procedure Methods 0.000 description 7
- 229940086542 triethylamine Drugs 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- YFCXQUJKPIVRBF-STBIYBPSSA-N 2-[(e)-1-[3-[[3-(4-methylpiperazin-1-yl)quinolin-6-yl]methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxyethanol Chemical compound C1CN(C)CCN1C1=CN=C(C=CC(CC=2N3N=C(C=CC3=NN=2)C(\C)=N\OCCO)=C2)C2=C1 YFCXQUJKPIVRBF-STBIYBPSSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 6
- 206010027476 Metastases Diseases 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 208000006265 Renal cell carcinoma Diseases 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 6
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 201000010279 papillary renal cell carcinoma Diseases 0.000 description 6
- 238000002953 preparative HPLC Methods 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
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Classifications
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- 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
-
- 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
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- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
- 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
- C07D471/06—Peri-condensed systems
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)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23544009P | 2009-08-20 | 2009-08-20 | |
| US61/235,440 | 2009-08-20 | ||
| CNPCT/CN2010/071978 | 2010-04-21 | ||
| CN2010071978 | 2010-04-21 | ||
| CNPCT/CN2010/074089 | 2010-06-18 | ||
| CN2010074089 | 2010-06-18 | ||
| PCT/EP2010/062057 WO2011020861A1 (en) | 2009-08-20 | 2010-08-18 | Heterocyclic oxime compounds |
Publications (1)
| Publication Number | Publication Date |
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| CA2771432A1 true CA2771432A1 (en) | 2011-02-24 |
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Family Applications (1)
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|---|---|---|---|
| CA2771432A Abandoned CA2771432A1 (en) | 2009-08-20 | 2010-08-18 | Heterocyclic oxime compounds |
Country Status (14)
| Country | Link |
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| US (2) | US8410264B2 (enExample) |
| EP (1) | EP2467383A1 (enExample) |
| JP (1) | JP5775871B2 (enExample) |
| KR (1) | KR20120089463A (enExample) |
| AR (1) | AR079486A1 (enExample) |
| AU (1) | AU2010284972A1 (enExample) |
| BR (1) | BR112012008061A2 (enExample) |
| CA (1) | CA2771432A1 (enExample) |
| EA (1) | EA201200318A1 (enExample) |
| IN (1) | IN2012DN01453A (enExample) |
| MX (1) | MX2012002179A (enExample) |
| TW (1) | TW201113284A (enExample) |
| UY (1) | UY32848A (enExample) |
| WO (1) | WO2011020861A1 (enExample) |
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-
2010
- 2010-08-18 CA CA2771432A patent/CA2771432A1/en not_active Abandoned
- 2010-08-18 EA EA201200318A patent/EA201200318A1/ru unknown
- 2010-08-18 AU AU2010284972A patent/AU2010284972A1/en not_active Abandoned
- 2010-08-18 JP JP2012525167A patent/JP5775871B2/ja not_active Expired - Fee Related
- 2010-08-18 EP EP10762878A patent/EP2467383A1/en not_active Withdrawn
- 2010-08-18 IN IN1453DEN2012 patent/IN2012DN01453A/en unknown
- 2010-08-18 BR BR112012008061A patent/BR112012008061A2/pt not_active Application Discontinuation
- 2010-08-18 MX MX2012002179A patent/MX2012002179A/es not_active Application Discontinuation
- 2010-08-18 WO PCT/EP2010/062057 patent/WO2011020861A1/en not_active Ceased
- 2010-08-18 KR KR1020127007032A patent/KR20120089463A/ko not_active Withdrawn
- 2010-08-19 AR ARP100103038A patent/AR079486A1/es unknown
- 2010-08-19 UY UY0001032848A patent/UY32848A/es unknown
- 2010-08-19 TW TW099127805A patent/TW201113284A/zh unknown
- 2010-08-19 US US12/859,653 patent/US8410264B2/en not_active Expired - Fee Related
-
2012
- 2012-08-06 US US13/567,386 patent/US8507676B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IN2012DN01453A (enExample) | 2015-06-05 |
| US8410264B2 (en) | 2013-04-02 |
| US8507676B2 (en) | 2013-08-13 |
| JP2013502396A (ja) | 2013-01-24 |
| MX2012002179A (es) | 2012-03-16 |
| KR20120089463A (ko) | 2012-08-10 |
| JP5775871B2 (ja) | 2015-09-09 |
| EA201200318A1 (ru) | 2012-09-28 |
| US20120302570A1 (en) | 2012-11-29 |
| WO2011020861A1 (en) | 2011-02-24 |
| US20110065708A1 (en) | 2011-03-17 |
| UY32848A (es) | 2011-03-31 |
| BR112012008061A2 (pt) | 2016-03-01 |
| EP2467383A1 (en) | 2012-06-27 |
| AR079486A1 (es) | 2012-02-01 |
| TW201113284A (en) | 2011-04-16 |
| AU2010284972A1 (en) | 2012-03-08 |
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